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inquiry10-chloro-5,5-difluoro-1,3,7,9-tetramethyl-5H-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinin-4-ium-5-uide
tetramethylstannane
4,4-difluoro-1,3,5,7,8-pentamethyl-4-bora-3a,4a-diaza-s-indecene
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0) In toluene for 5h; Stille Cross Coupling; Inert atmosphere; Reflux; | 97% |
2,4-dimethyl-1H-pyrrole
trifluoroborane diethyl ether
acetyl chloride
4,4-difluoro-1,3,5,7,8-pentamethyl-4-bora-3a,4a-diaza-s-indecene
Conditions | Yield |
---|---|
With N(CH2CH3)3 In dichloromethane addn. of acetyl chloride to pyrrole deriv. in CH2Cl2 at room temp. over 30 min, refluxing for 1 h, cooling, addn. to hexane, evapn., dissolving in CH2Cl2, addn. of amine deriv., stirring for 10 min at room temp., addn. of boron compd., stirring for 1 h; washing with aq. satd. soln. of Na2CO3, drying over Na2SO4, evapn., chromy. (silica, n-pentane/CH2Cl2 (1:1)), evapn., recrystn. (CH2Cl2/methanol), NMR and MS; | 72% |
2,4-dimethyl-1H-pyrrole
boron trifluoride diethyl etherate
acetyl chloride
4,4-difluoro-1,3,5,7,8-pentamethyl-4-bora-3a,4a-diaza-s-indecene
Conditions | Yield |
---|---|
Stage #1: 2,4-dimethyl-1H-pyrrole; acetyl chloride In dichloromethane at 20℃; for 1.5h; Stage #2: boron trifluoride diethyl etherate With triethylamine In dichloromethane at 20℃; for 1h; | 70% |
With triethylamine In dichloromethane | 68% |
Stage #1: 2,4-dimethyl-1H-pyrrole; acetyl chloride In dichloromethane for 1.5h; Inert atmosphere; Reflux; Stage #2: With triethylamine In dichloromethane for 0.25h; Inert atmosphere; Stage #3: boron trifluoride diethyl etherate In dichloromethane for 18h; Inert atmosphere; | 60% |
boron trifluoride diethyl etherate
4,4-difluoro-1,3,5,7,8-pentamethyl-4-bora-3a,4a-diaza-s-indecene
Conditions | Yield |
---|---|
In dichloromethane at 25℃; for 0.25h; | 70% |
5,5-difluoro-2,8-diiodo-1,3,7,9,10-pentamethyl-5H-4λ4,5λ4-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinine
dimethyl zinc(II)
A
4,4-difluoro-1,3,5,7,8-pentamethyl-4-bora-3a,4a-diaza-s-indecene
Conditions | Yield |
---|---|
With bis-triphenylphosphine-palladium(II) chloride In toluene at 20℃; for 0.666667h; Negishi Coupling; Schlenk technique; Sealed tube; Inert atmosphere; regioselective reaction; | A 9% B 69% |
2,4-dimethyl-1H-pyrrole
boron trifluoride diethyl etherate
4,4-difluoro-1,3,5,7,8-pentamethyl-4-bora-3a,4a-diaza-s-indecene
Conditions | Yield |
---|---|
Stage #1: 2,4-dimethyl-1H-pyrrole With acetyl chloride In dichloromethane at 20 - 50℃; for 1h; Stage #2: With triethylamine In hexane; dichloromethane at 20℃; for 0.166667h; Stage #3: boron trifluoride diethyl etherate In hexane; dichloromethane for 1h; | 58% |
2,4-dimethyl-1H-pyrrole
acetyl chloride
4,4-difluoro-1,3,5,7,8-pentamethyl-4-bora-3a,4a-diaza-s-indecene
Conditions | Yield |
---|---|
Stage #1: 2,4-dimethyl-1H-pyrrole; acetyl chloride In dichloromethane at 20℃; Inert atmosphere; Stage #2: With boron trifluoride diethyl etherate; triethylamine In dichloromethane | 40% |
With boron trifluoride diethyl etherate; triethylamine In dichloromethane | |
With boron trifluoride diethyl etherate; triethylamine In dichloromethane Inert atmosphere; |
tetrabutyl ammonium fluoride
4,4-difluoro-1,3,5,7,8-pentamethyl-4-bora-3a,4a-diaza-s-indecene
Conditions | Yield |
---|---|
In chloroform-d1 detected by NMR; |
3,5,3',5',6-pentamethyldipyrrin hydrochloride
4,4-difluoro-1,3,5,7,8-pentamethyl-4-bora-3a,4a-diaza-s-indecene
Conditions | Yield |
---|---|
Stage #1: 3,5,3',5',6-pentamethyldipyrrin hydrochloride With triethylamine In dichloromethane at 20℃; for 0.166667h; Stage #2: With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 1h; | 4.924 g |
C14H17BF(18)FN2
4,4-difluoro-1,3,5,7,8-pentamethyl-4-bora-3a,4a-diaza-s-indecene
Conditions | Yield |
---|---|
Heating; |
boron trifluoride diethyl etherate
4,4-difluoro-1,3,5,7,8-pentamethyl-4-bora-3a,4a-diaza-s-indecene
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20℃; for 0.166667h; |
2,4-dimethyl-1H-pyrrole
4,4-difluoro-1,3,5,7,8-pentamethyl-4-bora-3a,4a-diaza-s-indecene
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: dichloromethane 2: triethylamine / dichloromethane View Scheme | |
Multi-step reaction with 5 steps 1.1: toluene; diethyl ether / 1 h / 0 °C 2.1: potassium hydroxide; dihydrogen peroxide / ethanol; water / 0.08 h / Heating; Cooling with ice 3.1: phosgene / chloroform; toluene / 1 h / 20 °C 4.1: N-ethyl-N,N-diisopropylamine / chloroform / 0.5 h 4.2: 20 °C 5.1: tetrakis(triphenylphosphine) palladium(0) / toluene / 5 h / Inert atmosphere; Reflux View Scheme | |
Multi-step reaction with 2 steps 1: dichloromethane / 1 h / Reflux 2: triethylamine / dichloromethane / 0.17 h / 20 °C View Scheme |
boron trifluoride diethyl etherate
4,4-difluoro-1,3,5,7,8-pentamethyl-4-bora-3a,4a-diaza-s-indecene
Conditions | Yield |
---|---|
With triethylamine In dichloromethane |
bis-(3,5-dimethyl-1H-pyrrol-2-yl)methanone
4,4-difluoro-1,3,5,7,8-pentamethyl-4-bora-3a,4a-diaza-s-indecene
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: phosgene / chloroform; toluene / 1 h / 20 °C 2.1: N-ethyl-N,N-diisopropylamine / chloroform / 0.5 h 2.2: 20 °C 3.1: tetrakis(triphenylphosphine) palladium(0) / toluene / 5 h / Inert atmosphere; Reflux View Scheme |
bis(3,5-dimethyl-1H-pyrrol-2-yl)methanethione
4,4-difluoro-1,3,5,7,8-pentamethyl-4-bora-3a,4a-diaza-s-indecene
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: potassium hydroxide; dihydrogen peroxide / ethanol; water / 0.08 h / Heating; Cooling with ice 2.1: phosgene / chloroform; toluene / 1 h / 20 °C 3.1: N-ethyl-N,N-diisopropylamine / chloroform / 0.5 h 3.2: 20 °C 4.1: tetrakis(triphenylphosphine) palladium(0) / toluene / 5 h / Inert atmosphere; Reflux View Scheme |
4,4-difluoro-1,3,5,7,8-pentamethyl-4-bora-3a,4a-diaza-s-indecene
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: N-ethyl-N,N-diisopropylamine / chloroform / 0.5 h 1.2: 20 °C 2.1: tetrakis(triphenylphosphine) palladium(0) / toluene / 5 h / Inert atmosphere; Reflux View Scheme |
trimethylsilyl trifluoromethanesulfonate
4,4-difluoro-1,3,5,7,8-pentamethyl-4-bora-3a,4a-diaza-s-indecene
(CH3C(C4HN(CH3)2)2)BF(OSO2CF3)
Conditions | Yield |
---|---|
In toluene | 100% |
In chloroform-d1 monitored by NMR; | |
In toluene -25 °C; | |
In dichloromethane; acetonitrile at 20℃; for 0.0166667h; | |
20°C, 1 min; |
4,4-difluoro-1,3,5,7,8-pentamethyl-4-bora-3a,4a-diaza-s-indecene
5,5-difluoro-2,8-diiodo-1,3,7,9,10-pentamethyl-5H-4λ4,5λ4-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinine
Conditions | Yield |
---|---|
With N-iodo-succinimide In dichloromethane at 25℃; for 12h; | 100% |
With N-iodo-succinimide at 25℃; for 0.0166667h; Green chemistry; regioselective reaction; | 93% |
With N-iodo-succinimide; choline chloride at 25℃; for 0.25h; Green chemistry; | 92% |
4,4-difluoro-1,3,5,7,8-pentamethyl-4-bora-3a,4a-diaza-s-indecene
Conditions | Yield |
---|---|
In water-d2 at 80℃; for 1h; | 100% |
4,4-difluoro-1,3,5,7,8-pentamethyl-4-bora-3a,4a-diaza-s-indecene
Diethyl ketomalonate
Conditions | Yield |
---|---|
With piperidine; acetic acid In toluene at 60℃; | 100% |
2-(2-fluoropyridin-1-ium-1-yl)-1,1-bis((trifluoromethyl)sulfonyl)ethan-1-ide
4,4-difluoro-1,3,5,7,8-pentamethyl-4-bora-3a,4a-diaza-s-indecene
Conditions | Yield |
---|---|
In acetonitrile at 20℃; for 0.25h; Inert atmosphere; | 99.8% |
bromobenzene
4,4-difluoro-1,3,5,7,8-pentamethyl-4-bora-3a,4a-diaza-s-indecene
Conditions | Yield |
---|---|
With palladium diacetate; potassium carbonate; triphenylphosphine In 1,4-dioxane at 100℃; Reagent/catalyst; Inert atmosphere; | 99% |
methyl 2-{[(tert-butoxycarbonyl)oxy](phenyl)methyl}acrylate
4,4-difluoro-1,3,5,7,8-pentamethyl-4-bora-3a,4a-diaza-s-indecene
Conditions | Yield |
---|---|
With Cinchonidin In chloroform at 20℃; enantioselective reaction; | 99% |
methyl 2-(((tertbutoxycarbonyl)oxy)(4-chlorophenyl)methyl)acrylate
4,4-difluoro-1,3,5,7,8-pentamethyl-4-bora-3a,4a-diaza-s-indecene
Conditions | Yield |
---|---|
With Cinchonidin In chloroform at 20℃; enantioselective reaction; | 98% |
methyl 2-(((tertbutoxycarbonyl)oxy)(4-chlorophenyl)methyl)acrylate
4,4-difluoro-1,3,5,7,8-pentamethyl-4-bora-3a,4a-diaza-s-indecene
Conditions | Yield |
---|---|
With Cinchonin In chloroform at 20℃; enantioselective reaction; | 98% |
4,4-difluoro-1,3,5,7,8-pentamethyl-4-bora-3a,4a-diaza-s-indecene
1,1'-bi-2-naphthol
Conditions | Yield |
---|---|
Stage #1: 4,4-difluoro-1,3,5,7,8-pentamethyl-4-bora-3a,4a-diaza-s-indecene With aluminum (III) chloride In dichloromethane Reflux; Cooling with ether-dry ice; Stage #2: 1,1'-bi-2-naphthol In dichloromethane; acetonitrile at 20℃; for 18h; Inert atmosphere; | 97% |
4,4-difluoro-1,3,5,7,8-pentamethyl-4-bora-3a,4a-diaza-s-indecene
2,6-dibromo-4,4-difluoro-1,3,5,7-tetramethyl-8-methyl-4-bora-3a,4a-diaza-s-indacene
Conditions | Yield |
---|---|
With N-Bromosuccinimide at 25℃; for 0.0833333h; Green chemistry; regioselective reaction; | 95% |
With N-Bromosuccinimide; choline chloride at 25℃; Green chemistry; | 94% |
With bromine In dichloromethane at 20℃; Inert atmosphere; | 88% |
With bromine In dichloromethane at 20℃; for 3h; Inert atmosphere; | 88% |
methanesulfonic acid
4,4-difluoro-1,3,5,7,8-pentamethyl-4-bora-3a,4a-diaza-s-indecene
Conditions | Yield |
---|---|
In dichloromethane at 40℃; for 24h; | 92% |
N,N-dimethyl-formamide
4,4-difluoro-1,3,5,7,8-pentamethyl-4-bora-3a,4a-diaza-s-indecene
5,5-difluoro-1,3,7,9,10-pentamethyl-5H-5λ4,6λ4-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinine-2-carbaldehyde
Conditions | Yield |
---|---|
Stage #1: N,N-dimethyl-formamide With trichlorophosphate at 0 - 20℃; for 0.583333h; Inert atmosphere; Stage #2: 4,4-difluoro-1,3,5,7,8-pentamethyl-4-bora-3a,4a-diaza-s-indecene In 1,2-dichloro-ethane at 20 - 50℃; Inert atmosphere; | 89% |
With trichlorophosphate In 1,2-dichloro-ethane at 50℃; for 4h; Inert atmosphere; | 60% |
With trichlorophosphate In 1,2-dichloro-ethane at 60℃; |
trimethylsilylacetylene
4,4-difluoro-1,3,5,7,8-pentamethyl-4-bora-3a,4a-diaza-s-indecene
Conditions | Yield |
---|---|
Stage #1: trimethylsilylacetylene With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 1.5h; Inert atmosphere; Stage #2: 4,4-difluoro-1,3,5,7,8-pentamethyl-4-bora-3a,4a-diaza-s-indecene In tetrahydrofuran; hexane at 20℃; for 0.166667h; Inert atmosphere; | 89% |
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