3,5-Dimethylisoxazole-4-boronic acid → HCID 71259380, compound

HRID 1524433Notes

Reaction equation

HRID 1524433 reaction equation
[CH3:1][C:2]1[C:6](B(O)O)=[C:5]([CH3:10])[O:4][N:3]=1.Br[C:12]1[C:20]2[C:15](=[CH:16][C:17]([S:21]([N:24](CC3C=CC(OC)=CC=3OC)[C:25]3[S:29][N:28]=[CH:27][N:26]=3)(=[O:23])=[O:22])=[CH:18][CH:19]=2)[N:14]([CH3:41])[CH:13]=1>>[CH3:1][C:2]1[C:6]([C:12]2[C:20]3[C:15](=[CH:16][C:17]([S:21]([NH:24][C:25]4[S:29][N:28]=[CH:27][N:26]=4)(=[O:22])=[O:23])=[CH:18][CH:19]=3)[N:14]([CH3:41])[CH:13]=2)=[C:5]([CH3:10])[O:4][N:3]=1

Participants

3

Reactant 2

HCID 27343463,5-Dimethylisoxazole-4-boronic acidHCID 712592223-Bromo-N-(2,4-Dimethoxybenzyl)-1-Methyl-N-(1,2,4-Thiadiazol-5-yl)-1H-Indole-6-Sulfonamide

Product 1

HCID 71259380HCID 71259380, compound

Procedure

The title compound was prepared in an analogous manner to that described in Example 28 using (3,5-dimethylisoxazol-4-yl)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-(3,5-dimethylisoxazol-4-yl)-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 2.13 (s, 3 H) 2.31 (s, 3 H) 3.89 (s, 3 H) 7.41-7.49 (m, 2 H) 7.64 (s, 1 H) 7.90-7.93 (m, 1 H) 7.98 (s, 1 H). m/z (ESI) 389.1 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-7a569adda9b747859ef6aefd4b9c592e
Source dataset
uspto-grants-2015_07
Patent number
US09079902B2

Reaction notes

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