Sodium Bicarbonate → HCID 67141929, compound
Reaction equation
Cl.[F:2][C:3]1[CH:4]=[C:5]([CH:27]=[CH:28][CH:29]=1)[CH2:6][N:7]1[C:11]2=[C:12]([N:16]3[CH2:25][CH2:24][C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH2:17]3)[N:13]=[CH:14][CH:15]=[C:10]2[CH:9]=[C:8]1[CH3:26].C(=O)(O)[O-].[Na+]>>[F:2][C:3]1[CH:4]=[C:5]([CH:27]=[CH:28][CH:29]=1)[CH2:6][N:7]1[C:11]2=[C:12]([N:16]3[CH2:25][CH2:24][C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH2:17]3)[N:13]=[CH:14][CH:15]=[C:10]2[CH:9]=[C:8]1[CH3:26]Participants
Procedure
The compound prepared in Example 613 was treated with a saturated sodium bicarbonate solution to obtain 2-[1-(3-fluorobenzyl)-2-methyl-1H-pyrrolo[2,3-c]pyridin-7-yl]-1,2,3,4-tetrahydroisoquinoline. Morpholine (25 μl, 0.297 mmol), acetic acid (0.13 ml), and formaldehyde (70 μl) were added to a solution of 2-[1-(3-fluorobenzyl)-2-methyl-1H-pyrrolo[2,3-c]pyridin-7-yl]-1,2,3,4-tetrahydroisoquinoline (100 mg, 0.27 mmol) in ethanol (1.5 ml). The reaction mixture was refluxed overnight and then concentrated under reduced pressure. The resulting residue was dissolved in ethyl acetate and then washed with a sodium bicarbonate solution. The organic layer was dried on anhydrous magnesium sulfate and then concentrated under reduced pressure. The resulting residue was purified with silica gel column chromatography (ethyl acetate/dichloromethane=1/1, v/v) to give the titled compound as a pale yellow solid (Yield: 65%).
Sources & evidence
- ORD record
- ord-afad65c5d34241128b176f76ff8521a2
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08188114B2
Reaction notes
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