Phenylboronic Acid → HCID 71259526, compound

HRID 1524426Notes

Reaction equation

[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:11]1[C:19]2[C:14](=[CH:15][C:16]([S:20]([N:23](CC3C=CC(OC)=CC=3OC)[C:24]3[S:28][N:27]=[CH:26][N:25]=3)(=[O:22])=[O:21])=[CH:17][CH:18]=2)[N:13]([CH3:40])[CH:12]=1>>[CH3:40][N:13]1[C:14]2[C:19](=[CH:18][CH:17]=[C:16]([S:20]([NH:23][C:24]3[S:28][N:27]=[CH:26][N:25]=3)(=[O:21])=[O:22])[CH:15]=2)[C:11]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:12]1

Participants

Reactant 2

HCID 66827Phenylboronic Acid

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

Product 1

HCID 71259526HCID 71259526, compound

Procedure

The title compound was prepared in an analogous manner to that described in Example 28 using phenylboronic 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-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 3.88 (s, 3 H) 7.15-7.30 (m, 1 H) 7.43 (t, J=7.73 Hz, 2 H) 7.48-7.55 (m, 1 H) 7.61-7.68 (m, 2 H) 7.81 (d, J=4.47 Hz, 2 H) 7.85-7.89 (m, 2 H). m/z (ESI) 370.1 (M+H)+.

Workup

customThe title compound was prepared in an analogous manner to that

Sources & evidence

ORD record: ord-bb65e9d8cc7c415a84c2385a8ceccf68
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09079902B2

Reaction notes

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