Quinolin-5-ylboronic acid → HCID 71259367, compound

HRID 1524429Notes

Reaction equation

HRID 1524429 reaction equation
[N:1]1[C:10]2[C:5](=[C:6](B(O)O)[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.Br[C:15]1[C:23]2[C:18](=[CH:19][C:20]([S:24]([N:27](CC3C=CC(OC)=CC=3OC)[C:28]3[S:32][N:31]=[CH:30][N:29]=3)(=[O:26])=[O:25])=[CH:21][CH:22]=2)[N:17]([CH3:44])[CH:16]=1>>[CH3:44][N:17]1[C:18]2[C:23](=[CH:22][CH:21]=[C:20]([S:24]([NH:27][C:28]3[S:32][N:31]=[CH:30][N:29]=3)(=[O:25])=[O:26])[CH:19]=2)[C:15]([C:6]2[CH:7]=[CH:8][CH:9]=[C:10]3[C:5]=2[CH:4]=[CH:3][CH:2]=[N:1]3)=[CH:16]1

Participants

3

Reactant 2

HCID 5153389Quinolin-5-ylboronic acidHCID 712592223-Bromo-N-(2,4-Dimethoxybenzyl)-1-Methyl-N-(1,2,4-Thiadiazol-5-yl)-1H-Indole-6-Sulfonamide

Product 1

HCID 71259367HCID 71259367, compound

Procedure

The title compound was prepared in an analogous manner to that described in Example 28 using quinolin-5-ylboronic 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-3-(quinolin-5-yl)-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 3.99 (s, 3 H) 7.43-7.51 (m, 3 H) 7.64-7.68 (m, 1 H) 7.82-7.89 (m, 2 H) 8.01-8.05 (m, 2 H) 8.20 (s, 1 H) 8.33 (d, J=8.02 Hz, 1 H) 8.93 (dd, J=4.12, 1.60 Hz, 1 H). m/z (ESI) 421.1 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-2679c33a1b914f6789aedb0c1af690e4
Source dataset
uspto-grants-2015_07
Patent number
US09079902B2

Reaction notes

Loading…