CAS No.17274-65-6,5-BROMO-N,N-DIMETHYLTRYPTAMINE Suppliers

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2-(5-bromo-1H-indol-3-yl)-N,N-dimethylethanamine

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Synthetic route

: 19718-92-4
4-(N,N-dimethylamino)butyraldehyde dimethyl acetal

: 622-88-8
4-bromophenylhydrazine hydrochloride

: 17274-65-6
5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole

Conditions

Conditions	Yield
With sulfuric acid for 2h; Heating;	93%

: 717139-78-1
2-(5-bromo-3-hydroxy-2-oxo-2,3-dihydro-1H-indol-3-yl)-N,N-dimethyl-acetamide

A: 4-amino-2-(2-amino-5-bromo-phenyl)-4-dimethyl-butan-1-ol

B: 17274-65-6
5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole

Conditions

Conditions	Yield
Stage #1: 2-(5-bromo-3-hydroxy-2-oxo-2,3-dihydro-1H-indol-3-yl)-N,N-dimethyl-acetamide With sodium tetrahydroborate; boron trifluoride diethyl etherate In 1,2-dimethoxyethane at 25 - 27℃; for 12h; Stage #2: With 4 N NAOH In 1,2-dimethoxyethane at 80℃; for 0.5h; Stage #3: With 1,2-diaza-bicyclo[2.2.2]octane In 1,2-dimethoxyethane for 2h;	A n/a B 85%

: 717139-78-1
2-(5-bromo-3-hydroxy-2-oxo-2,3-dihydro-1H-indol-3-yl)-N,N-dimethyl-acetamide

: 17274-65-6
5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole

Conditions

Conditions	Yield
Stage #1: 2-(5-bromo-3-hydroxy-2-oxo-2,3-dihydro-1H-indol-3-yl)-N,N-dimethyl-acetamide With sodium tetrahydroborate; boron trifluoride diethyl etherate In 1,2-dimethoxyethane at -15 - 20℃; Stage #2: With 1,4-diaza-bicyclo[2.2.2]octane for 2h; Heating / reflux; Stage #3: With manganese(IV) oxide; sodium hydroxide; water more than 3 stages;	85%

: 67-56-1
methanol

: 3610-42-2
5-bromotryptamine

: 17274-65-6
5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole

Conditions

Conditions	Yield
With formaldehyd; nitrogen; sodium cyanoborohydride; acetic acid at 0 - 20℃; for 24h;	84%

: 199658-93-0
2-(5-bromo-1H-indol-3-yl)-N,N-dimethyl-2-oxoacetamide

: 17274-65-6
5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole

Conditions

Conditions	Yield
With sodium hydroxide In tetrahydrofuran; hexane; ethyl acetate	75%
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; Heating / reflux;

: 50-00-0
formaldehyd

: 3610-42-2
5-bromotryptamine

: 17274-65-6
5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole

Conditions

Conditions	Yield
With sodium acetate; sodium cyanoborohydride In methanol at 0 - 25℃; for 5h;	70.4%

: 10075-50-0
5-bromo-1H-indole

: 108-01-0
2-(N,N-dimethylamino)ethanol

: 17274-65-6
5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole

Conditions

Conditions	Yield
With C37H36Cl2NPRuS2; caesium carbonate at 135℃; for 24h; Inert atmosphere; Sealed tube;	40%

: 161202-91-1
1-hydroxy-N,N-dimethyltryptamine

A: 61-50-7
N,N-dimethyltryptamine

B: 17274-65-6
5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole

C: 2-bromo-N,N-dimethyltryptamine

Conditions

Conditions	Yield
With hydrogen bromide for 1h; Ambient temperature;	A 11% B 25% C 2%

...Expand

: 199658-93-0
2-(5-bromo-1H-indol-3-yl)-N,N-dimethyl-2-oxoacetamide

A: 61-50-7
N,N-dimethyltryptamine

B: 17274-65-6
5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In 1,4-dioxane for 3h; Heating;

: 3610-42-2
5-bromotryptamine

: 74-88-4
methyl iodide

: 17274-65-6
5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole

Conditions

Conditions	Yield
Stage #1: 5-bromotryptamine With vinylsulfonylmethyl polystyrene In N,N-dimethyl-formamide Stage #2: methyl iodide In N,N-dimethyl-formamide Stage #3: With N-ethyl-N,N-diisopropylamine In dichloromethane Hoffman elimination; Further stages.;

: 120-72-9
indole

(+-)-indolin-3-ol: (+-)-indolin-3-ol

: 17274-65-6
5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 87 percent 2: 70 percent / LiAlH4 3: 92 percent / triethylsilane, CF3COOH 4: 55 percent / Na2WO4*2H2O, 30percent H2O2 / methanol; H2O 5: 25 percent / 47percent aq. HBr / 1 h / Ambient temperature View Scheme

: 61-50-7
N,N-dimethyltryptamine

: 17274-65-6
5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 92 percent / triethylsilane, CF3COOH 2: 55 percent / Na2WO4*2H2O, 30percent H2O2 / methanol; H2O 3: 25 percent / 47percent aq. HBr / 1 h / Ambient temperature View Scheme

: 29095-44-1
2-(1H-indol-3-yl)-N,N-dimethyl-2-oxoacetamide

: 17274-65-6
5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 70 percent / LiAlH4 2: 92 percent / triethylsilane, CF3COOH 3: 55 percent / Na2WO4*2H2O, 30percent H2O2 / methanol; H2O 4: 25 percent / 47percent aq. HBr / 1 h / Ambient temperature View Scheme

: 38662-17-8, 79867-87-1
2-(dihydroindol-3-yl)-N,N-dimethylethylamine

: 17274-65-6
5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 55 percent / Na2WO4*2H2O, 30percent H2O2 / methanol; H2O 2: 25 percent / 47percent aq. HBr / 1 h / Ambient temperature View Scheme

: 10075-50-0
5-bromo-1H-indole

: 17274-65-6
5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: diethyl ether / 0 °C 2: H2O / 0.5 h 3: LiAlH4 / dioxane / 3 h / Heating View Scheme

: 63843-81-2
2-(5-bromo-1H-indol-3-yl)-2-oxoacetyl chloride

: 17274-65-6
5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: H2O / 0.5 h 2: LiAlH4 / dioxane / 3 h / Heating View Scheme

: 1116-77-4
4,4-diethoxy-N,N-dimethyl-1-butanamine

: 622-88-8
4-bromophenylhydrazine hydrochloride

: 17274-65-6
5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole

Conditions

Conditions	Yield
Stage #1: 4,4-diethoxy-N,N-dimethyl-1-butanamine; 4-bromophenylhydrazine hydrochloride With acetic acid In water for 4h; Fischer Indole Synthesis; Reflux; Stage #2: With sodium hydrogencarbonate In water pH=8 - 9;

: 50-00-0
formaldehyd

: 81868-12-4
2-(5-bromo-1H-indol-3-yl)ethanamine hydrochloride

: 17274-65-6
5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole

Conditions

Conditions	Yield
With sodium methylate; sodium cyanoborohydride; acetic acid In methanol; water at 20℃;

: 17274-65-6
5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole

: 61-50-7
N,N-dimethyltryptamine

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal In methanol for 18h;	100%

: 17274-65-6
5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole

: 1294480-65-1
5-bromo-3-[2-(N,N-dimethylamino)ethyl]-3-fluoro-2-oxoindole

Conditions

Conditions	Yield
With aluminum (III) chloride; Selectfluor In methanol; acetonitrile at 0 - 20℃; for 0.5h;	95%

: 51599-68-9
1-(methylsulfonyl)-pyrrolidine

: 17274-65-6
5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole

: 154323-57-6
almotriptan

Conditions

Conditions	Yield
With nickel dichloride; lithium tert-butoxide; nixantphos In tetrahydrofuran at 0 - 80℃; for 13h; Reagent/catalyst; Inert atmosphere;	92%

: 17274-65-6
5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole

: 74-88-4
methyl iodide

: 5-bromo-N,N,N-trimethyltryptamine

Conditions

Conditions	Yield
In chloroform at 0 - 20℃;	88%

: 17274-65-6
5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole

: 17380-42-6
N,N-dimethyl 2-(5-cyano-1H-indol-3-yl)ethylamine

Conditions

Conditions	Yield
With 1,1'-bis(diphenylphosphino)ferrocene; zink cyanide; tris(dibenzylideneacetone)dipalladium(0) chloroform complex In DMF (N,N-dimethyl-formamide) at 110℃; for 21h;	84%

: 557-21-1
dicyanozinc

: 17274-65-6
5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole

: 17380-42-6
N,N-dimethyl 2-(5-cyano-1H-indol-3-yl)ethylamine

Conditions

Conditions	Yield
1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0) In DMF (N,N-dimethyl-formamide); chloroform at 110℃; for 21h; Product distribution / selectivity;	84%
With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; zinc In hexanes; N,N-dimethyl-formamide at 20 - 60℃; for 0.75h;	37.6%

methanolic ammonia: methanolic ammonia

: 17274-65-6
5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole

: 98-88-4
benzoyl chloride

: 208464-42-0
5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1-benzoylindole

Conditions

Conditions	Yield
With dmap In dichloromethane; triethylamine	84%

...Expand

: 17274-65-6
5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole

: 98-88-4
benzoyl chloride

: 208464-42-0
5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1-benzoylindole

Conditions

Conditions	Yield
With triethylamine; dmap In dichloromethane at 20℃; for 20h;	84%

: 17274-65-6
5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole

: 152673-51-3
3-[2-(Dimethylamino)ethyl]-1H-indole-5-carboxaldehyde

Conditions

Conditions	Yield
With tert.-butyl lithium In DMF (N,N-dimethyl-formamide); hexane at -75 - -30℃; for 1.33333h;	81.8%

: 17274-65-6
5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole

: [2-(1-benzyl-5-bromo-1H-indol-3-yl)-ethyl]-dimethyl-amine

Conditions

Conditions	Yield
With sodium hydride; benzyl chloride In DMF (N,N-dimethyl-formamide)	76.6%

: 4039-82-1
Benzyl propargyl ether

: 17274-65-6
5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole

: 717139-86-1
{2-[5-(3-benzyloxy-prop-1-ynyl)-1H-indol-3-yl]-ethyl}-dimethyl-amine

Conditions

Conditions	Yield
With piperidine; tri-tert-butyl phosphine; copper(I) iodide; dichloro bis(acetonitrile) palladium(II) In hexane at 50℃; for 20h;	75%

: 17274-65-6
5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole

: 99505-03-0
5-amino-3-(2-dimethylaminoethyl)-1H-indol

Conditions

Conditions	Yield
Stage #1: 5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole With tris-(dibenzylideneacetone)dipalladium(0) In tetrahydrofuran at 20℃; for 0.0833333h; Stage #2: With lithium hexamethyldisilazane In tetrahydrofuran at 20℃; for 21h; Heating / reflux; Stage #3: With hydrogenchloride; sodium hydroxide; water more than 3 stages;	74.1%

: 17274-65-6
5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole

: 1310827-05-4
C12H15BrN2O

Conditions

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In chloroform at 0℃; for 0.166667h; Inert atmosphere;	73%

: 17274-65-6
5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole

: 208464-59-9
C17H24N2OS

Conditions

Conditions	Yield
	34%

: 17274-65-6
5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole

: 3-[2-(N,N-Dimethylamino)ethyl]-5-(4-hydroxytetrahydropyran-4-yl)-1H-indole

Conditions

Conditions	Yield
	30%

: 17274-65-6
5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole

: 5-(1-Aza-1-methyl-4-hydroxycyclohex-4-yl)-3-[2-(N,N-dimethylamino)ethyl]-1H-indole

Conditions

Conditions	Yield
With tert.-butyl lithium; potassium hydride In tetrahydrofuran	20%

: 17274-65-6
5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole

: 3-(2-dimethylamino-ethyl)-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1,3-dihydro-indol-2-one

Conditions

Conditions	Yield
Stage #1: 5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole With tert.-butyl lithium In diethyl ether; pentane at -78 - -30℃; for 1.25h; Stage #2: With 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In diethyl ether; pentane at -30 - -25℃; for 0.5h; Stage #3: In diethyl ether; chloroform; water; pentane at 20℃; for 1.5h;	15.3%

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Antimex Chemical Limied

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coolpharm Ltd

Debye Scientific

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