(4-Methoxynaphthalen-1-yl)boronic acid → HCID 71259210, compound

HRID 1524431Notes

Reaction equation

HRID 1524431 reaction equation
[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6](B(O)O)=[CH:5][CH:4]=1.Br[C:17]1[C:25]2[C:20](=[CH:21][C:22]([S:26]([N:29](CC3C=CC(OC)=CC=3OC)[C:30]3[S:34][N:33]=[CH:32][N:31]=3)(=[O:28])=[O:27])=[CH:23][CH:24]=2)[N:19]([CH3:46])[CH:18]=1>>[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([C:17]2[C:25]3[C:20](=[CH:21][C:22]([S:26]([NH:29][C:30]4[S:34][N:33]=[CH:32][N:31]=4)(=[O:27])=[O:28])=[CH:23][CH:24]=3)[N:19]([CH3:46])[CH:18]=2)=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 4198749(4-Methoxynaphthalen-1-yl)boronic acidHCID 712592223-Bromo-N-(2,4-Dimethoxybenzyl)-1-Methyl-N-(1,2,4-Thiadiazol-5-yl)-1H-Indole-6-Sulfonamide

Product 1

HCID 71259210HCID 71259210, compound

Procedure

The title compound was prepared in an analogous manner to that described in Example 28 using (4-methoxynaphthalen-1-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-(4-methoxynaphthalen-1-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 3.96 (s, 3 H) 4.02 (s, 3 H) 7.06 (d, J=8.02 Hz, 1 H) 7.32 (d, J=8.36 Hz, 1 H) 7.37-7.48 (m, 3 H) 7.51 (d, J=8.25 Hz, 1 H) 7.72 (s, 1 H) 7.84 (d, J=8.59 Hz, 1 H) 7.97 (s, 1 H) 8.13 (s, 1 H) 8.24 (d, J=8.36 Hz, 1 H). m/z (ESI) 450.1 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-24d28f279b6f41fc83a8e1e18b186e98
Source dataset
uspto-grants-2015_07
Patent number
US09079902B2

Reaction notes

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