Water → HCID 18407044, compound
Reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]2[C:12]([CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])=[C:11]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=3)[NH:10][C:7]2=[N:8][CH:9]=1.I[CH3:27].O>CN(C)C=O>[Cl:3][C:4]1[CH:5]=[C:6]2[C:12]([CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])=[C:11]([C:19]3[CH:20]=[CH:21][C:22]([Cl:25])=[CH:23][CH:24]=3)[N:10]([CH3:27])[C:7]2=[N:8][CH:9]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
Sodium hydride (60% suspension in mineral oil, 15 mg, 0.38 mmol) was added to a stirred, cooled (0° C.) solution of methyl 5-chloro-2-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine-3-propanoate (Description 4, 82 mg, 0.23 mmol) in dimethylformamide (5 mL) and the mixture was stirred at room temperature for 10 min. Iodomethane (24 μL, 54 mg, 0.38 mmol) was added and the mixture was stirred at room temperature for 5 min. Water (15 mL) was added and the mixture was extracted with ethyl acetate (3×15 mL). The combined organic fractions were washed with brine, dried (MgSO4) and the solvent was evaporated under reduced pressure to give the title compound (82 mg, 96%). 1H NMR (360 MHz, CDCl3) δ 8.27 (1H, d, J 2.2 Hz), 7.87 (1H, d, J 2.2 Hz), 7.50 (2H, m), 7.34 (2H, m), 3.64 (3H, s), 3.60 (3H, s), 2.98 (2H, t, J 7.8 Hz), and 2.51 (2H, t, J 7.8 Hz).
Workup
- stirringthe mixture was stirred at room temperature for 5 min
- extractionthe mixture was extracted with ethyl acetate (3×15 mL)
- washThe combined organic fractions were washed with brine
- dry with materialdried (MgSO4)
- customthe solvent was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-0770b621288f4f3cb04032604d92b1f7
- Source dataset
- uspto-grants-2002_11
- Patent number
- US06476045B2
Reaction notes
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