3-(Trifluoromethoxy)phenylboronic Acid (contains varying amounts of Anhydride) → 1-methyl-N-(1,2,4-thiadiazol-5-yl)-3-(3-(trifluoromethoxy)phenyl)-1H-indole-6-sulfonamide

HRID 1524424Notes

Reaction equation

HRID 1524424 reaction equation
[F:1][C:2]([F:14])([F:13])[O:3][C:4]1[CH:5]=[C:6](B(O)O)[CH:7]=[CH:8][CH:9]=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:6]2[CH:7]=[CH:8][CH:9]=[C:4]([O:3][C:2]([F:14])([F:13])[F:1])[CH:5]=2)=[CH:17]1

Participants

3

Reactant 2

HCID 27343853-(Trifluoromethoxy)phenylboronic Acid (contains varying amounts of Anhydride)HCID 712592223-Bromo-N-(2,4-Dimethoxybenzyl)-1-Methyl-N-(1,2,4-Thiadiazol-5-yl)-1H-Indole-6-Sulfonamide

Product 1

HCID 712594721-methyl-N-(1,2,4-thiadiazol-5-yl)-3-(3-(trifluoromethoxy)phenyl)-1H-indole-6-sulfonamide

Procedure

The title compound was prepared in an analogous manner to that described in Example 28 using (3-(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-(3-(trifluoromethoxy)phenyl)-1H-indole-6-sulfonamide, was isolated as an off-white solid. 1H NMR (500 MHz, DMSO-d6) δ ppm 3.89 (s, 3 H) 7.22 (d, J=8.25 Hz, 1 H) 7.54-7.58 (m, 3 H) 7.71 (d, J=8.02 Hz, 1 H) 7.87-7.92 (m, 3 H) 7.98 (s, 1 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-79e22c82115f40ac85529fddd95a1a9f
Source dataset
uspto-grants-2015_07
Patent number
US09079902B2

Reaction notes

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