5-(1H-indol-2-yl)-2,4-dimethoxybenzaldehyde → 4-{3E-[5-(1H-Indol-2-yl)-2,4-dimethoxyphenyl]acryloyl}-N-pyridin-2-ylbenzenesulfonamide

Reaction equation

[C:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)(=[O:12])=[O:11])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].C([N:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[C:24]1[C:32]1[C:33]([O:42][CH3:43])=[CH:34][C:35]([O:40][CH3:41])=[C:36]([CH:39]=1)[CH:37]=O)(=O)C.N1C2C(=CC=CC=2)C=C1C1C(OC)=CC(OC)=C(C=1)C=O>>[NH:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[C:24]1[C:32]1[C:33]([O:42][CH3:43])=[CH:34][C:35]([O:40][CH3:41])=[C:36](/[CH:37]=[CH:2]/[C:1]([C:4]2[CH:5]=[CH:6][C:7]([S:10]([NH:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=3)(=[O:12])=[O:11])=[CH:8][CH:9]=2)=[O:3])[CH:39]=1

Participants

Reactant 3

HCID 161156215-(1H-indol-2-yl)-2,4-dimethoxybenzaldehyde

HCID 210825305-(1-acetyl-1H-indol-2-yl)-2,4-dimethoxybenzaldehyde

HCID 227503274-Acetyl-N-(2-pyridyl)benzenesulfonamide

Product 1

HCID 112380194-{3E-[5-(1H-Indol-2-yl)-2,4-dimethoxyphenyl]acryloyl}-N-pyridin-2-ylbenzenesulfonamide

Procedure

NH4Cl (25 mL) and transferred to a separatory funnel containing THF (50 mL), EtOAc (50 mL) and H2O (50 mL). The layers were cut and the organic layer was concentrated to dryness. The crude product was suspended in EtOH (50 mL), filtered and then dried under vacuum to afford 2.5 g (85% yield) of the title compound, analytical dada identical as above. Similarly, the title compound could be prepared from 4-acetyl-N-pyridin-2-ylbenzenesulfonamide (Ex-5A) and 5-(1-acetyl-1H-indol-2-yl)-2,4-dimethoxybenzaldehyde (Ex-57F) or 5-(1H-indol-2-yl)-2,4-dimethoxybenzaldehyde (Ex-57D or Ex-57DD).