2-Chloro-4-methoxybenzeneboronic acid → HCID 71259483, compound

HRID 1524432Notes

Reaction equation

HRID 1524432 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1B(O)O.Br[C:14]1[C:22]2[C:17](=[CH:18][C:19]([S:23]([N:26](CC3C=CC(OC)=CC=3OC)[C:27]3[S:31][N:30]=[CH:29][N:28]=3)(=[O:25])=[O:24])=[CH:20][CH:21]=2)[N:16]([CH3:43])[CH:15]=1>>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:14]1[C:22]2[C:17](=[CH:18][C:19]([S:23]([NH:26][C:27]3[S:31][N:30]=[CH:29][N:28]=3)(=[O:24])=[O:25])=[CH:20][CH:21]=2)[N:16]([CH3:43])[CH:15]=1

Participants

3

Reactant 2

HCID 27733302-Chloro-4-methoxybenzeneboronic acidHCID 712592223-Bromo-N-(2,4-Dimethoxybenzyl)-1-Methyl-N-(1,2,4-Thiadiazol-5-yl)-1H-Indole-6-Sulfonamide

Product 1

HCID 71259483HCID 71259483, compound

Procedure

The title compound was prepared in an analogous manner to that described in Example 28 using (2-chloro-4-methoxyphenyl)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-chloro-4-methoxyphenyl)-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 3.82 (s, 3 H) 3.92 (s, 3 H) 6.96-7.04 (m, 1 H) 7.17 (d, J=2.63 Hz, 1 H) 7.42 (d, J=8.59 Hz, 1 H) 7.45-7.53 (m, 2 H) 7.71 (s, 1 H) 7.93 (s, 1 H) 8.19 (s, 1 H). m/z (ESI) 434.0 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-fbd9bc692ede42efb6f890ebc27ef018
Source dataset
uspto-grants-2015_07
Patent number
US09079902B2

Reaction notes

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