2,4-Dimethoxybenzeneboronic acid → HCID 71259574, compound

HRID 1524427Notes

Reaction equation

HRID 1524427 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1B(O)O.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:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[C:15]1[C:23]2[C:18](=[CH:19][C:20]([S:24]([NH:27][C:28]3[S:32][N:31]=[CH:30][N:29]=3)(=[O:25])=[O:26])=[CH:21][CH:22]=2)[N:17]([CH3:44])[CH:16]=1

Participants

3

Reactant 2

HCID 27343412,4-Dimethoxybenzeneboronic acidHCID 712592223-Bromo-N-(2,4-Dimethoxybenzyl)-1-Methyl-N-(1,2,4-Thiadiazol-5-yl)-1H-Indole-6-Sulfonamide

Product 1

HCID 71259574HCID 71259574, compound

Procedure

The title compound was prepared in an analogous manner to that described in Example 28 using (2,4-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-(2,4-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 3.76 (s, 3H) 3.80 (s, 3H) 3.87 (s, 3H) 6.59-6.68 (m, 2 H) 7.35 (d, J=8.25 Hz, 1 H) 7.43 (dd, J=8.42, 1.43 Hz, 1 H) 7.52-7.60 (m, 1 H) 7.85 (s, 1 H) 7.94 (br. s., 1 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-a20cc372d38d431da81d40e24ea8ec09
Source dataset
uspto-grants-2015_07
Patent number
US09079902B2

Reaction notes

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