[CH3:1][CH:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1.C([O-])([O-])=O.[K+].[K+].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[NH4+].[Cl-]>CN(C=O)C.CCOCC>[CH2:17]([N:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH2:10][CH:2]1[CH3:1])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1
To a solution of 1 g (7.5 mmol) of 2-methyl-2,3-dihydro-1H-indole in anhydrous DMF were added 1.03 g (7.5 mmol) of K2CO3 and then dropwise 0.97 mL (8.0 mmol) of benzylbromide. The mixture was stirred at RT for 3hrs and then distributed between Et2O and a saturated aqueous solution of NH4Cl. The combined organic phases were dried over Na2SO4 and evaporated to yield 1.7 g (quantitative) of crude 1-benzyl-2-methyl-2,3-dihydro-1H-indole, light blue oil, MS: 224 (MH+).
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