4-(Trifluoromethoxy)phenylboronic acid → 1-methyl-N-(1,2,4-thiadiazol-5-yl)-3-(4-(trifluoromethoxy)phenyl)-1H-indole-6-sulfonamide

HRID 1524423Notes

Reaction equation

HRID 1524423 reaction equation
[F:1][C:2]([F:14])([F:13])[O:3][C:4]1[CH:9]=[CH:8][C:7](B(O)O)=[CH:6][CH:5]=1.Br[C:16]1[C:24]2[C:19](=[CH:20][C:21]([S:25]([N:28](CC3C=CC(OC)=CC=3OC)[C:29]3[S:33][N:32]=[CH:31][N:30]=3)(=[O:27])=[O:26])=[CH:22][CH:23]=2)[N:18]([CH3:45])[CH:17]=1>>[CH3:45][N:18]1[C:19]2[C:24](=[CH:23][CH:22]=[C:21]([S:25]([NH:28][C:29]3[S:33][N:32]=[CH:31][N:30]=3)(=[O:26])=[O:27])[CH:20]=2)[C:16]([C:7]2[CH:8]=[CH:9][C:4]([O:3][C:2]([F:14])([F:13])[F:1])=[CH:5][CH:6]=2)=[CH:17]1

Participants

3

Reactant 2

HCID 27343864-(Trifluoromethoxy)phenylboronic acidHCID 712592223-Bromo-N-(2,4-Dimethoxybenzyl)-1-Methyl-N-(1,2,4-Thiadiazol-5-yl)-1H-Indole-6-Sulfonamide

Product 1

HCID 712594591-methyl-N-(1,2,4-thiadiazol-5-yl)-3-(4-(trifluoromethoxy)phenyl)-1H-indole-6-sulfonamide

Procedure

The title compound was prepared in an analogous manner to that described in Example 28 using (4-(trifluoromethoxy)phenyl)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, 1-methyl-N-(1,2,4-thiadiazol-5-yl)-3-(4-(trifluoromethoxy)phenyl)-1H-indole-6-sulfonamide, was isolated as an off-white solid. 1H NMR (500 MHz, DMSO-d6) δ ppm 3.90 (s, 3 H) 7.41 (m, J=8.13 Hz, 2 H) 7.52-7.58 (m, 1 H) 7.74-7.79 (m, 2 H) 7.88-8.00 (m, 4 H). m/z (ESI) 454.0 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-2564a74a191d4adc94d8c2ccd0adff01
Source dataset
uspto-grants-2015_07
Patent number
US09079902B2

Reaction notes

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