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

HRID 1524421Notes

Reaction equation

HRID 1524421 reaction equation
[C:1]([C:3]1[CH:4]=[C:5](B(O)O)[CH:6]=[CH:7][C:8]=1[F:9])#[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:4]=[C:5]([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:6]=[CH:7][C:8]=1[F:9])#[N:2]

Participants

3

Reactant 2

HCID 27579643-Cyano-4-fluorophenylboronic acidHCID 712592223-Bromo-N-(2,4-Dimethoxybenzyl)-1-Methyl-N-(1,2,4-Thiadiazol-5-yl)-1H-Indole-6-Sulfonamide

Product 1

HCID 712592263-(3-cyano-4-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 (3-cyano-4-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-(3-cyano-4-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 3.90 (s, 3 H) 7.54-7.60 (m, 2 H) 7.91-8.07 (m, 5 H) 8.13 (dd, J=6.13, 2.35 Hz, 1H). 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-42db842207214c05bebec5002c098314
Source dataset
uspto-grants-2015_07
Patent number
US09079902B2

Reaction notes

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