(3,5-Dimethoxyphenyl)boronic acid → 3-(3,5-dimethoxyphenyl)-1-methyl-N-(1,2,4-thiadiazol-5-yl)-1H-indole-6-sulfonamide

HRID 1524420Notes

Reaction equation

HRID 1524420 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5](B(O)O)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.Br[C:15]1[C:23]2[C:18](=[CH:19][C:20]([S:24]([N:27](CC3C=CC(OC)=CC=3OC)[C:28]3[S:32][N:31]=[CH:30][N:29]=3)(=[O:26])=[O:25])=[CH:21][CH:22]=2)[N:17]([CH3:44])[CH:16]=1>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:15]2[C:23]3[C:18](=[CH:19][C:20]([S:24]([NH:27][C:28]4[S:32][N:31]=[CH:30][N:29]=4)(=[O:25])=[O:26])=[CH:21][CH:22]=3)[N:17]([CH3:44])[CH:16]=2)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1

Participants

3

Reactant 2

HCID 4374257(3,5-Dimethoxyphenyl)boronic acidHCID 712592223-Bromo-N-(2,4-Dimethoxybenzyl)-1-Methyl-N-(1,2,4-Thiadiazol-5-yl)-1H-Indole-6-Sulfonamide

Product 1

HCID 712597293-(3,5-dimethoxyphenyl)-1-methyl-N-(1,2,4-thiadiazol-5-yl)-1H-indole-6-sulfonamide

Procedure

The title compound was prepared in an analogous manner to that described in Example 28 using (3,5-dimethoxyphenyl)boronic acid and 3-bromo-N-(2,4-dimethoxybenzyl)-1-methyl-N-(1,2,4-thiadiazol-5-yl)-1H-indole-6-sulfonamide, and the desired product, 3-(3,5-dimethoxyphenyl)-1-methyl-N-(1,2,4-thiadiazol-5-yl)-1H-indole-6-sulfonamide, was isolated as an off-white solid. 1H NMR (500 MHz, DMSO-d6) δ ppm 3.78-3.88 (m, 9 H) 6.39 (t, J=2.23 Hz, 1 H) 6.77 (d, J=2.29 Hz, 2 H) 7.52 (dd, J=8.42, 1.55 Hz, 1 H) 7.75-7.89 (m, 4 H). m/z (ESI) 430.1 (M+H)+.

Workup

  1. customThe title compound was prepared in an analogous manner to that

Sources & evidence

ORD record
ord-d5efffac44e14ebb9bcd947d5ff58fc3
Source dataset
uspto-grants-2015_07
Patent number
US09079902B2

Reaction notes

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