Dimethylformamide → 1-Biphenyl-2-ylmethyl-4-methoxy-2-methyl-1H-pyrrolo[3,2-c]pyridine
Reaction equation
[CH3:1][O:2][C:3]1[C:8]2[CH:9]=[C:10]([CH3:12])[NH:11][C:7]=2[CH:6]=[CH:5][N:4]=1.CN(C=O)C.[C:18]1([C:24]2[CH:31]=[CH:30][CH:29]=[CH:28][C:25]=2[CH2:26]Br)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>>[C:24]1([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:31]=[CH:30][CH:29]=[CH:28][C:25]=1[CH2:26][N:11]1[C:7]2[CH:6]=[CH:5][N:4]=[C:3]([O:2][CH3:1])[C:8]=2[CH:9]=[C:10]1[CH3:12]Participants
4
Procedure
To a solution of intermediate (3) (0.70 g, 4.69 mmole) in anhydrous DMF (40 mL) sodium hydride (60% in mineral oil, 0.28 g, 7.04 mmole) was added, the mixture was stirred for 1 h. To the mixture 2-phenylbenzyl bromide (0.95 mL, 5.16 mmole) was added dropwise. The mixture was stirred at room temperature for 18 h. The reaction was quenched with saturated ammonium chloride solution (200 mL), the mixture was extracted with ethyl acetate (3×200 mL). The organic layer was separated and washed with water, dried over magnesium sulphate and concentrated. The residue was purified by column chromatography (3:1 Hex:EtOAc) to afford intermediate (4) as a yellow solid. Yield: 1.1 g 71%.
Workup
- stirringThe mixture was stirred at room temperature for 18 h
- customThe reaction was quenched with saturated ammonium chloride solution (200 mL)
- extractionthe mixture was extracted with ethyl acetate (3×200 mL)
- customThe organic layer was separated
- washwashed with water
- dry with materialdried over magnesium sulphate
- concentrationconcentrated
- customThe residue was purified by column chromatography (3:1 Hex:EtOAc)
Sources & evidence
- ORD record
- ord-cafadc17bb8c459caa254967b5e7c061
- Source dataset
- uspto-grants-2010_02
- Patent number
- US07666898B2
Reaction notes
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