2-Methoxyphenylboronic acid → 4-fluoro-1-(2-methoxyphenyl)-N-(1,2,4-thiadiazol-5-yl)isoquinoline-6-sulfonamide

HRID 1473600Notes

Reaction equation

HRID 1473600 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([S:12]([N:15](CC3C=CC(OC)=CC=3OC)[C:16]3[S:20][N:19]=[CH:18][N:17]=3)(=[O:14])=[O:13])=[CH:9][CH:10]=2)[C:5]([F:32])=[CH:4][N:3]=1.[CH3:33][O:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1B(O)O>>[F:32][C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[C:8]([S:12]([NH:15][C:16]3[S:20][N:19]=[CH:18][N:17]=3)(=[O:13])=[O:14])[CH:7]=2)[C:2]([C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=2[O:34][CH3:33])=[N:3][CH:4]=1

Participants

3

Reactant 2

HCID 27339582-Methoxyphenylboronic acidHCID 866876631-chloro-N-(2,4-dimethoxybenzyl)-4-fluoro-N-(1,2,4-thiadiazol-5-yl)isoquinoline-6-sulfonamide

Product 1

HCID 866876644-fluoro-1-(2-methoxyphenyl)-N-(1,2,4-thiadiazol-5-yl)isoquinoline-6-sulfonamide

Procedure

The title compound was prepared in an analogous manner to that of EXAMPLE 228, except that 1-chloro-N-(2,4-dimethoxybenzyl)-4-fluoro-N-(1,2,4-thiadiazol-5-yl)isoquinoline-6-sulfonamide and (2-methoxyphenyl)boronic acid were used as the coupling partners. The final compound was purified via column chromatography (RediSep Gold 12 g silica gel column, gradient elution 0-10% MeOH:DCM) to afford 4-fluoro-1-(2-methoxyphenyl)-N-(1,2,4-thiadiazol-5-yl)isoquinoline-6-sulfonamide as a grey solid. 1H NMR (400 MHz, DMSO-d6) δ=8.72 (s, 1H), 8.49 (s, 2H), 8.01 (dd, J=1.5, 8.9 Hz, 1H), 7.80 (d, J=9.2 Hz, 1H), 7.61-7.51 (m, 1H), 7.33 (dd, J=1.4, 7.4 Hz, 1H), 7.23 (d, J=8.2 Hz, 1H), 7.18-7.08 (m, 1H), 3.65 (s, 3H). m/z (ESI) 417.2 (M+H)+.

Workup

  1. customThe title compound was prepared in an analogous manner to that of EXAMPLE 228
  2. customThe final compound was purified via column chromatography (RediSep Gold 12 g silica gel column, gradient elution 0-10% MeOH:DCM)

Sources & evidence

ORD record
ord-6c81649206f94194bb11d10b5e865966
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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