Conditions | Yield |
---|---|
With dihydrogen peroxide; trifluoroacetic anhydride In dichloromethane; water at 0 - 20℃; | 57% |
Stage #1: 2,3-difluoroanilline With tetrafluoroboric acid; sodium nitrite In water at 0℃; for 1.33333h; Stage #2: With copper In water for 1.33333h; | 25% |
triethylsilane
2,3,4-trifluoronitrobenzene
A
triethylsilyl fluoride
B
1,2-difluoro-3-nitrobenzene
Conditions | Yield |
---|---|
With dmap; (1,3-bis(2,4,6-trimethylphenyl)imidazolin-2-ylidene)AuH In dichloromethane at 40℃; for 12h; Inert atmosphere; | A n/a B 53% |
Conditions | Yield |
---|---|
With 4,5-bis-(di-tert-butyl-phosphanyl)-9,9-dimethyl-9H-xanthene; [t-BuXantphosAu]+[Cl-Au-Cl]-; diphenylsilane; acetic acid In 1,2-dichloro-ethane at 80℃; for 24h; Inert atmosphere; | 12 %Spectr. |
2,3,4-trifluoronitrobenzene
A
3,4-difluoronitrobenzene
B
1,2-difluoro-3-nitrobenzene
C
2,3,4-trifluoroaniline
Conditions | Yield |
---|---|
With Dimethylphenylsilane; o-phenylenebis(diphenylphosphine); potassium tert-butylate; copper(l) chloride In tetrahydrofuran for 12h; Inert atmosphere; Reflux; Overall yield = 95 %Spectr.; regioselective reaction; |
1,2-difluoro-3-nitrobenzene
methylamine
2-fluoro-N-methyl-6-nitroaniline
Conditions | Yield |
---|---|
With potassium carbonate In 1,4-dioxane; ethanol at 20℃; Inert atmosphere; | 100% |
With lithium aluminium tetrahydride In methanol; ethanol at 70℃; for 0.75h; Inert atmosphere; Sealed tube; UV-irradiation; | 100% |
In methanol; ethanol at 70℃; for 0.5h; Microwave heating; |
1,2-difluoro-3-nitrobenzene
phenylmethanethiol
2-(benzylsulfanyl)-1-fluoro-3-nitrobenzene
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 2h; regioselective reaction; | 99% |
tert-butyl N-methyl-N-(piperidin-4-ylmethyl)carbamate
1,2-difluoro-3-nitrobenzene
tert-butyl (1-(2-fluoro-6-nitrophenyl)piperidin-4-yl)methyl(methyl)carbamate
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In acetonitrile at 80℃; for 18h; | 99% |
1,2-difluoro-3-nitrobenzene
ethanolamine
2-[(2-fluoro-6-nitrophenyl)amino]ethanol
Conditions | Yield |
---|---|
In ethanol at 20℃; | 97% |
isonipecotic acid methyl ester
1,2-difluoro-3-nitrobenzene
methyl 1-(2-fluoro-6-nitrophenyl)piperidine-4-carboxylate
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In acetonitrile at 80℃; | 97% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 65℃; | 90% |
1,2-difluoro-3-nitrobenzene
methyl 3-aminopropanoate hydrochloride
3-(2-fluoro-6-nitrophenylamino)propionic acid methyl ester
Conditions | Yield |
---|---|
With potassium fluoride; 18-crown-6 ether; N-ethyl-N,N-diisopropylamine In acetonitrile for 2h; Heating / reflux; | 86% |
Conditions | Yield |
---|---|
With NaH; ammonium chloride; trifluoroacetic acid In dichloromethane; N,N-dimethyl-formamide | A 85% B n/a |
1,2-difluoro-3-nitrobenzene
Cyclopropylamine
N-cyclopropyl-2-fluoro-6-nitroaniline
Conditions | Yield |
---|---|
In ethanol at 20℃; for 16h; Inert atmosphere; | 81% |
1,2-difluoro-3-nitrobenzene
4-benzyloxyphenylhydrazide
Conditions | Yield |
---|---|
In dimethyl sulfoxide at 100℃; for 10h; | 81% |
1,2-difluoro-3-nitrobenzene
glycine ethyl ester hydrochloride
(2-fluoro-6-nitrophenylamino)acetic acid ethyl ester
Conditions | Yield |
---|---|
With potassium fluoride; 18-crown-6 ether; N-ethyl-N,N-diisopropylamine In acetonitrile for 3h; Heating / reflux; | 73% |
(R)-piperidin-3-ylcarbamic acid tert-butyl ester
1,2-difluoro-3-nitrobenzene
C16H22FN3O4
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In acetonitrile at 80℃; | 72% |
Conditions | Yield |
---|---|
Stage #1: (S)-N-(tert-butoxycarbonyl)serine With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 1.16667h; Stage #2: 1,2-difluoro-3-nitrobenzene In N,N-dimethyl-formamide; mineral oil at 0℃; for 2h; | 68% |
1,2-difluoro-3-nitrobenzene
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In acetonitrile at 80℃; for 12h; | 59% |
Conditions | Yield |
---|---|
With caesium carbonate In N,N-dimethyl-formamide at 80℃; for 16h; | 56.9% |
1,2-difluoro-3-nitrobenzene
Conditions | Yield |
---|---|
Stage #1: 1,2-difluoro-3-nitrobenzene With sulfuric acid; silver sulfate at 20℃; for 0.0833333h; Stage #2: With bromine at 20℃; for 16h; | 55% |
With N-Bromosuccinimide; sulfuric acid at 60℃; for 6h; | 34.51% |
1,2-difluoro-3-nitrobenzene
malonic acid dimethyl ester
2-(2-fluoro-6-nitrophenyl)malonic acid dimethyl ester
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 65℃; for 24h; | 43% |
With potassium carbonate In N,N-dimethyl-formamide at 65℃; for 24h; | 43% |
1,2-difluoro-3-nitrobenzene
aniline
(2-fluoro-6-nitrophenyl)phenylamine
Conditions | Yield |
---|---|
With caesium carbonate In dimethyl sulfoxide at 20 - 90℃; for 7h; | 39% |
1,2-difluoro-3-nitrobenzene
methyl 5-amino-2-pyridinecarboxylate
Conditions | Yield |
---|---|
With caesium carbonate In dimethyl sulfoxide at 18 - 25℃; for 5h; | 27% |
1,2-difluoro-3-nitrobenzene
guanidine nitrate
5-fluoro-1,2,4-benzotriazine-3-amine 1-oxide
Conditions | Yield |
---|---|
With potassium tert-butylate 1.) THF, 60 deg C, 6 h, 2.) THF, 2 h; Yield given. Multistep reaction; |
formaldehyd
Glyoxal
1,2-difluoro-3-nitrobenzene
2-chloro-4,4-difluoro-4,5-dihydrospiro[5H-thieno[2,3-c]pyran-7,4'-piperidine]
3-methyl-1H-pyrazole-4-carbaldehyde
2-chloro-4,4-difluoro-1'-[[1-(2-fluoro-6-imidazol-1-yl-phenyl)-3-methyl-pyrazol-4-yl]methyl]spiro[5H-thieno[2,3-c]pyran-7,4'-piperidine]
Conditions | Yield |
---|---|
Stage #1: 1,2-difluoro-3-nitrobenzene; 3-methyl-1H-pyrazole-4-carbaldehyde With potassium carbonate In acetonitrile at 20℃; Stage #2: 2-chloro-4,4-difluoro-4,5-dihydrospiro[5H-thieno[2,3-c]pyran-7,4'-piperidine] In dichloromethane at 20℃; for 0.5h; Stage #3: formaldehyd; Glyoxal |
1,2-difluoro-3-nitrobenzene
3-methyl-1H-pyrazole-4-carbaldehyde
methyl chloroformate
methyl iodide
A
methyl N-[3-fluoro-2-(4-formyl-3-methyl-pyrazol-1-yl)phenyl]-N-methyl-carbamate
Conditions | Yield |
---|---|
Stage #1: 1,2-difluoro-3-nitrobenzene; 3-methyl-1H-pyrazole-4-carbaldehyde With potassium carbonate In acetonitrile at 20℃; Stage #2: With iron; acetic acid In ethanol; water at 90℃; for 2h; Stage #3: methyl chloroformate; methyl iodide |
1,2-difluoro-3-nitrobenzene
2-chloro-4,4-difluoro-4,5-dihydrospiro[5H-thieno[2,3-c]pyran-7,4'-piperidine]
3-methyl-1H-pyrazole-4-carbaldehyde
methyl chloroformate
methyl iodide
methyl N-[2-[4-[(2-chloro-4,4-difluoro-spiro[5H-thieno[2,3-c]pyran-7,4'-piperidine]-1'-yl)methyl]-3-methyl-pyrazol-1-yl]-3-fluoro-phenyl]-N-methyl-carbamate
Conditions | Yield |
---|---|
Stage #1: 1,2-difluoro-3-nitrobenzene; 3-methyl-1H-pyrazole-4-carbaldehyde With potassium carbonate In acetonitrile at 20℃; Stage #2: With iron; acetic acid In ethanol; water at 90℃; for 2h; Stage #3: 2-chloro-4,4-difluoro-4,5-dihydrospiro[5H-thieno[2,3-c]pyran-7,4'-piperidine]; methyl chloroformate; methyl iodide |
1,2-difluoro-3-nitrobenzene
3-methyl-1H-pyrazole-4-carbaldehyde
methyl chloroformate
methyl N-[3-fluoro-2-(4-formyl-3-methyl-pyrazol-1-yl)phenyl]carbamate
Conditions | Yield |
---|---|
Stage #1: 1,2-difluoro-3-nitrobenzene; 3-methyl-1H-pyrazole-4-carbaldehyde With potassium carbonate In acetonitrile at 20℃; Stage #2: With iron; acetic acid In ethanol; water at 90℃; for 2h; Stage #3: methyl chloroformate With pyridine In dichloromethane at 0 - 20℃; for 0.5h; |
1,2-difluoro-3-nitrobenzene
3-methyl-1H-pyrazole-4-carbaldehyde
B
1-(2-amino-6-fluoro-phenyl)-3-methyl-1H-pyrazole-4-carbaldehyde
Conditions | Yield |
---|---|
Stage #1: 1,2-difluoro-3-nitrobenzene; 3-methyl-1H-pyrazole-4-carbaldehyde With potassium carbonate In acetonitrile at 20℃; Stage #2: With iron; acetic acid In ethanol; water at 90℃; for 2h; |
1,2-difluoro-3-nitrobenzene
3-methyl-1H-pyrazole-4-carbaldehyde
B
1-(2-fluoro-6-nitro-phenyl)-3-methyl-1H-pyrazole-4-carbaldehyde
Conditions | Yield |
---|---|
With potassium carbonate In acetonitrile at 20℃; |
1,2-difluoro-3-nitrobenzene
2-chloro-4,4-difluoro-4,5-dihydrospiro[5H-thieno[2,3-c]pyran-7,4'-piperidine]
3-methyl-1H-pyrazole-4-carbaldehyde
A
2-chloro-4,4-difluoro-1'-[[1-(2-fluoro-6-nitro-phenyl)-3-methyl-pyrazol-4-yl]methyl]spiro[5H-thieno[2,3-c]pyran-7,4'-piperidine]
Conditions | Yield |
---|---|
Stage #1: 1,2-difluoro-3-nitrobenzene; 3-methyl-1H-pyrazole-4-carbaldehyde With potassium carbonate In acetonitrile at 20℃; Stage #2: 2-chloro-4,4-difluoro-4,5-dihydrospiro[5H-thieno[2,3-c]pyran-7,4'-piperidine] In dichloromethane at 20℃; for 0.5h; Stage #3: With sodium tris(acetoxy)borohydride In dichloromethane at 20℃; |
1,2-difluoro-3-nitrobenzene
2-chloro-4,4-difluoro-4,5-dihydrospiro[5H-thieno[2,3-c]pyran-7,4'-piperidine]
3-methyl-1H-pyrazole-4-carbaldehyde
B
2-[4-[(2-chloro-4,4-difluoro-spiro[5H-thieno[2,3-c]pyran-7,4'-piperidine]-1'-yl)methyl]-3-methyl-pyrazol-1-yl]-3-fluoro-aniline
Conditions | Yield |
---|---|
Stage #1: 1,2-difluoro-3-nitrobenzene; 3-methyl-1H-pyrazole-4-carbaldehyde With potassium carbonate In acetonitrile at 20℃; Stage #2: 2-chloro-4,4-difluoro-4,5-dihydrospiro[5H-thieno[2,3-c]pyran-7,4'-piperidine] In dichloromethane at 20℃; for 0.5h; |
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