Sodium Bicarbonate → HCID 11551838, compound
Reaction equation
Cl.[CH2:2]([C:5]1[C:9]2[C:10]([N:14]3[CH2:23][CH2:22][C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[CH2:15]3)=[N:11][CH:12]=[CH:13][C:8]=2[NH:7][C:6]=1[CH3:24])[CH:3]=[CH2:4].C(=O)(O)[O-].[Na+]>>[CH2:2]([C:5]1[C:9]2[C:10]([N:14]3[CH2:23][CH2:22][C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[CH2:15]3)=[N:11][CH:12]=[CH:13][C:8]=2[NH:7][C:6]=1[CH3:24])[CH:3]=[CH2:4]Participants
Procedure
The compound (20 mg, 0.056 mmol) prepared in Example 81 was treated with a saturated sodium bicarbonate solution to obtain 3-allyl-2-methyl-4-(1,2,3,4-tetrahydroisoquinolin-2-yl)-1H-pyrrolo[3,2-c]pyridine (14 mg, 0.054 mmol). Sodium hydride (60%, 4.3 mg, 0.108 mmol) was added at room temperature to a solution of 3-allyl-2-methyl-4-(1,2,3,4-tetrahydroisoquinolin-2-yl)-1H-pyrrolo[3,2-c]pyridine (14 mg, 0.054 mmol) in N,N-dimethylformamide (1 ml) and then the reaction mixture was stirred for 30 minutes. Iodomethane (0.004 ml, 0.06 mmol) was added to the reaction mixture, which was then stirred for 1 hour at room temperature. The reaction mixture was diluted with ethyl acetate (10 ml) and washed with water (10 ml) three times. The organic layer was separated, dried on anhydrous magnesium sulfate, and then concentrated. The resulting residue was dissolved in ethyl acetate (1 ml), saturated with hydrochloric acid gas, and then filtered to give the titled compound as a white solid. (Yield: 42.3%)
Sources & evidence
- ORD record
- ord-0e1adf53e6d44cfba4f9719aa276d884
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08513277B2
Reaction notes
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