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Dimethylformamide → 1-[Bis(4-fluorophenyl)methyl]-2-formyl-4,6-dimethyl-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile

HRID 730434
Notes
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Reaction equation

HRID 730434 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.CCCCCC.[F:19][C:20]1[CH:25]=[CH:24][C:23]([CH:26]([C:40]2[CH:45]=[CH:44][C:43]([F:46])=[CH:42][CH:41]=2)[N:27]2[C:31]3=[N:32][C:33]([CH3:37])=[CH:34][C:35]([CH3:36])=[C:30]3[C:29]([C:38]#[N:39])=[CH:28]2)=[CH:22][CH:21]=1.CN(C)[CH:49]=[O:50]>O1CCCC1.O>[F:46][C:43]1[CH:42]=[CH:41][C:40]([CH:26]([C:23]2[CH:24]=[CH:25][C:20]([F:19])=[CH:21][CH:22]=2)[N:27]2[C:31]3=[N:32][C:33]([CH3:37])=[CH:34][C:35]([CH3:36])=[C:30]3[C:29]([C:38]#[N:39])=[C:28]2[CH:49]=[O:50])=[CH:45][CH:44]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 5

HCID 6228DimethylformamideHCID 7912DiisopropylamineHCID 8058HexaneHCID 690625951-[Bis(4-fluorophenyl)methyl]-4,6-dimethyl-1H-pyrrolo[2,3-b]pyridine-3-carbonitrileHCID 178418339Butyllithium

Product 1

HCID 86760956
1-[Bis(4-fluorophenyl)methyl]-2-formyl-4,6-dimethyl-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of diisopropylamine (5.27 ml, 40.2 mmol) in tetrahydrofuran (50 ml) was added a 1.6 N solution of butyllithium in hexane (25.1 ml, 40.2 mmol) at −78° C., which was stirred at −78° C. for 15 minutes. To the resultant solution was added dropwise 1-[bis(4-fluorophenyl)methyl]-4,6-dimethyl-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile (11.6 g, 31.1 mmol) at −78° C., and the mixture was stirred at −78° C. for 30 minutes. Dimethylformamide (6.23 ml, 80.4 mmol) was added thereto, and the mixture was stirred at room temperature for 1.5 hours, poured into iced water and extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to give the objective product as a solid material.

Workup

  1. stirringthe mixture was stirred at −78° C. for 30 minutes
  2. stirringthe mixture was stirred at room temperature for 1.5 hours
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-a6318c43e97a4c3a9d59ac3ab2e91a55
Source dataset
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07582651B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes