3-Cyanophenylboronic acid → HCID 71259691, compound

HRID 1524425Notes

Reaction equation

HRID 1524425 reaction equation
[C:1]([C:3]1[CH:4]=[C:5](B(O)O)[CH:6]=[CH:7][CH:8]=1)#[N:2].Br[C:13]1[C:21]2[C:16](=[CH:17][C:18]([S:22]([N:25](CC3C=CC(OC)=CC=3OC)[C:26]3[S:30][N:29]=[CH:28][N:27]=3)(=[O:24])=[O:23])=[CH:19][CH:20]=2)[N:15]([CH3:42])[CH:14]=1>>[C:1]([C:3]1[CH:4]=[C:5]([C:13]2[C:21]3[C:16](=[CH:17][C:18]([S:22]([NH:25][C:26]4[S:30][N:29]=[CH:28][N:27]=4)(=[O:23])=[O:24])=[CH:19][CH:20]=3)[N:15]([CH3:42])[CH:14]=2)[CH:6]=[CH:7][CH:8]=1)#[N:2]

Participants

3

Reactant 2

HCID 27343253-Cyanophenylboronic acidHCID 712592223-Bromo-N-(2,4-Dimethoxybenzyl)-1-Methyl-N-(1,2,4-Thiadiazol-5-yl)-1H-Indole-6-Sulfonamide

Product 1

HCID 71259691HCID 71259691, compound

Procedure

The title compound was prepared in an analogous manner to that described in Example 28 using (3-cyanophenyl)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-cyanophenyl)-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) 7.56 (dd, J=8.48, 1.60 Hz, 1 H) 7.61-7.69 (m, 2 H) 7.86-7.92 (m, 2 H) 7.94-8.07 (m, 4 H). m/z (ESI) 395.1 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-b585d6b7553b49979b9eecfd30a0f4d4
Source dataset
uspto-grants-2015_07
Patent number
US09079902B2

Reaction notes

Loading…