Dimethylformamide → HCID 86760949, compound
Reaction equation
C(NC(C)C)(C)C.C([Li])CCC.CCCCCC.[CH3:19][C:20]1[CH:25]=[C:24]([CH3:26])[N:23]=[C:22]2[N:27]([C@H:32]3[C:41]4[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=4)[CH2:35][CH2:34][CH2:33]3)[CH:28]=[C:29]([C:30]#[N:31])[C:21]=12.CN(C)[CH:44]=[O:45]>O1CCCC1.O>[CH:44]([C:28]1[N:27]([C@H:32]2[C:41]3[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=3)[CH2:35][CH2:34][CH2:33]2)[C:22]2=[N:23][C:24]([CH3:26])=[CH:25][C:20]([CH3:19])=[C:21]2[C:29]=1[C:30]#[N:31])=[O:45]Participants
Conditions
- Temperature
- -78 °C
Procedure
To a solution of diisopropylamine (3.72 ml, 28.4 mmol) in tetrahydrofuran (36 ml) was added a 1.6 N solution of butyllithium in hexane (17.7 ml, 28.4 mmol) at −78° C., and the mixture was stirred at −78° C. for 15 minutes. To the resultant solution was added dropwise 4,6-dimethyl-1-[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile (5.70 g, 18.9 mmol) in THF (60 ml) at −78° C., and the mixture was stirred at −78° C. for 30 minutes. Dimethylformamide (5.37 ml, 56.7 mmol) was added thereto, and the mixture was stirred at room temperature 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 oily matter.
Workup
- stirringthe mixture was stirred at −78° C. for 30 minutes
- stirringthe mixture was stirred at room temperature 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
- customto give the objective product as oily matter
Sources & evidence
- ORD record
- ord-7851c3a0bb1d4819b32254ee0b673126
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07582651B2
Reaction notes
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