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. Dimethylamine (2.0M in tetrahydrofuran solution; 378 μl, 0.75 mmol), acetic acid (0.03 ml), and formaldehyde (163 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 (234 mg, 0.63 mmol) in ethanol (3.5 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). The resulting product was dissolved in ethyl acetate, saturated with hydrochloric acid gas, and then filtered to give the titled compound as a white solid (Yield: 68%).
Sources & evidence
- ORD record
- ord-69fbaf2717a6486e87f62620068e22e6
- Source dataset
- uspto-grants-2010_02
- Patent number
- US07662832B2
Reaction notes
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