3-(Methylsulfonyl)phenylboronic acid → HCID 71259411, compound

HRID 1524430Notes

Reaction equation

HRID 1524430 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[C:7](B(O)O)[CH:8]=[CH:9][CH:10]=1)(=[O:4])=[O:3].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:7]2[CH:8]=[CH:9][CH:10]=[C:5]([S:2]([CH3:1])(=[O:4])=[O:3])[CH:6]=2)=[CH:16]1

Participants

3

Reactant 2

HCID 27735423-(Methylsulfonyl)phenylboronic acidHCID 712592223-Bromo-N-(2,4-Dimethoxybenzyl)-1-Methyl-N-(1,2,4-Thiadiazol-5-yl)-1H-Indole-6-Sulfonamide

Product 1

HCID 71259411HCID 71259411, compound

Procedure

The title compound was prepared in an analogous manner to that described in Example 28 using (3-(methylsulfonyl)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-3-(3-(methylsulfonyl)phenyl)-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 3.91 (s, 3 H) 7.57 (dd, J=8.48, 1.49 Hz, 1 H) 7.71 (t, J=7.73 Hz, 1 H) 7.77 (d, J=8.02 Hz, 1 H) 7.84-7.95 (m, 3 H) 8.02 (d, J=7.90 Hz, 2 H) 8.05 (s, 1 H) 8.13 (s, 1 H). m/z (ESI) 448.0 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-e87f551dd44e4afca58f4bc61a3680d4
Source dataset
uspto-grants-2015_07
Patent number
US09079902B2

Reaction notes

Loading…