Sodium Bicarbonate → HCID 11523067, compound
Reaction equation
Cl.[CH2:2]([N:5]1[C:9]2=[C:10]([CH2:14][NH:15][C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[N:11]=[CH:12][CH:13]=[C:8]2[C:7]([CH3:23])=[C:6]1[CH3:24])[CH:3]=[CH2:4].C(=O)(O)[O-].[Na+]>>[CH2:2]([N:5]1[C:9]2=[C:10]([CH2:14][NH:15][C:16]3[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=3)[N:11]=[CH:12][CH:13]=[C:8]2[C:7]([CH3:23])=[C:6]1[CH3:24])[CH:3]=[CH2:4]Participants
Procedure
The compound prepared in Example 88 was treated with a saturated sodium bicarbonate solution to obtain N-(1-allyl-2,3-dimethyl-1H-pyrrolo[2,3-c]pyridin-7-ylmethyl)-4-fluorophenylamine. A solution of N-(1-allyl-2,3-dimethyl-1H-pyrrolo[2,3-c]pyridin-7-ylmethyl)-4-fluorophenylamine (40 mg, 0.13 mmol) and sodium hydride (60%, 7.8 mg, 0.19 mmol) in anhydrous N,N-dimethylformamide (5 ml) was stirred overnight at room temperature. The reaction mixture was diluted with ethyl acetate (15 ml), washed with water (20 ml), dried on anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was purified with silica gel column chromatography (ethyl acetate/n-hexane=1/1, v/v). The resulting yellow oil was dissolved in ethyl acetate, saturated with hydrochloric acid gas, and then filtered. The resulting solid was dried under reduced pressure to give 3.3 mg of the titled compound as a white solid.
Sources & evidence
- ORD record
- ord-7e4c40ed7e7346328d92cc43a4c194f7
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08188114B2
Reaction notes
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