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

HRID 1524422Notes

Reaction equation

HRID 1524422 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][C:4]=1[F:12])#[N:2].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>>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:14]2[C:22]3[C:17](=[CH:18][C:19]([S:23]([NH:26][C:27]4[S:31][N:30]=[CH:29][N:28]=4)(=[O:24])=[O:25])=[CH:20][CH:21]=3)[N:16]([CH3:43])[CH:15]=2)=[CH:5][C:4]=1[F:12])#[N:2]

Participants

3

Reactant 2

HCID 2783130(4-Cyano-3-fluorophenyl)boronic acidHCID 712592223-Bromo-N-(2,4-Dimethoxybenzyl)-1-Methyl-N-(1,2,4-Thiadiazol-5-yl)-1H-Indole-6-Sulfonamide

Product 1

HCID 712595173-(4-cyano-3-fluorophenyl)-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 (4-cyano-3-fluorophenyl)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-(4-cyano-3-fluorophenyl)-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 3.92 (s, 3 H) 7.60 (dd, J=8.53, 1.55 Hz, 1 H) 7.73-7.80 (m, 2 H) 7.87-7.97 (m, 2 H) 8.02-8.10 (m, 2 H) 8.23 (s, 1 H). m/z (ESI) 413.0 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-788a7cedf0544b0d8c13247d059d03f5
Source dataset
uspto-grants-2015_07
Patent number
US09079902B2

Reaction notes

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