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

HRID 730434Notes

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

Participants

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

stirringthe mixture was stirred at −78° C. for 30 minutes
stirringthe mixture was stirred at room temperature for 1.5 hours
extractionextracted with ethyl acetate
washThe extract was washed with water
dry with materialdried over anhydrous magnesium sulfate
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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