[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]#[N:11])=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.CN(C)C1C=CC=CC=1.Cl[CH:22]([CH3:26])[C:23](Cl)=[O:24].C(Cl)[Cl:28]>O>[Cl:28][CH2:26][CH2:22][C:23]([N:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]#[N:11])=[CH:7][CH:8]=2)[CH2:3][CH2:2]1)=[O:24]To a solution of 2,3-dihydro-1H-indole-5-carbonitrile (8 g, 0.0556 mol; see step (iv) above) in DCM (50 mL) at 0° C. was added N,N-dimethylaniline (13.5 g, 0.1112 mol) followed by 2-chloropropionyl chloride (8.46 g, 0.0667 mol). The reaction mixture was stirred for 3 h before being diluted with water and extracted with DCM. The organic layer was washed with water and brine, dried over sodium sulfate and then concentrated under reduced pressure. The resulting residue was purified by column chromatography over silica gel to yield the sub-title compound as a pale yellow solid. Yield: 10.5 g.
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