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

HRID 347387Notes

Reaction equation

HRID 347387 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

4

Reactant 3

HCID 161156215-(1H-indol-2-yl)-2,4-dimethoxybenzaldehydeHCID 210825305-(1-acetyl-1H-indol-2-yl)-2,4-dimethoxybenzaldehydeHCID 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).

Sources & evidence

ORD record
ord-278ea6195e5c4f0e9b60dd8cba55d90c
Source dataset
uspto-grants-2007_02
Patent number
US07173129B2

Reaction notes

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