(2-Methoxypyridin-3-yl)boronic acid → HCID 86687667, compound

HRID 1473603Notes

Reaction equation

HRID 1473603 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:17][CH:18]=[CH:19][N:20]=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[C:40](B(O)O)=[CH:39][CH:38]=[CH:37][N:36]=1>>[F:32][C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[C:8]([S:12]([NH:15][C:16]3[S:17][CH:18]=[CH:19][N:20]=3)(=[O:14])=[O:13])[CH:7]=2)[C:2]([C:40]2[C:35]([O:34][CH3:33])=[N:36][CH:37]=[CH:38][CH:39]=2)=[N:3][CH:4]=1

Participants

3

Reactant 2

HCID 2762709(2-Methoxypyridin-3-yl)boronic acidHCID 86687426HCID 86687426, compound

Product 1

HCID 86687667HCID 86687667, compound

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-(thiazol-2-yl)isoquinoline-6-sulfonamide and 2-methoxy-3-pyridineboronic 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-methoxypyridin-3-yl)-N-(thiazol-2-yl)isoquinoline-6-sulfonamide as a white solid. 1H NMR (400 MHz, DMSO-d6) δ=13.00 (br. s., 1H), 8.73 (d, J=1.3 Hz, 1H), 8.51 (d, J=1.3 Hz, 1H), 8.39 (dd, J=1.9, 4.9 Hz, 1H), 8.01 (dd, J=1.7, 8.9 Hz, 1H), 7.87-7.76 (m, 2H), 7.31 (d, J=4.6 Hz, 1H), 7.22 (dd, J=5.0, 7.2 Hz, 1H), 6.90 (d, J=4.5 Hz, 1H), 3.77 (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-78126fa1bd854525a532aab2bb502fa2
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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