3-(Methylsulfonyl)phenylboronic acid → 1-(1,3-Dimethyl-1H-pyrazol-4-yl)-8-(3-methanesulfonyl-phenyl)-3-methyl-1,3-dihydro-imidazo[4,5-c]quinolin-2-one

HRID 445588Notes

Reaction equation

HRID 445588 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[N:12]([CH3:23])[C:13](=[O:22])[N:14]([C:15]4[C:16]([CH3:21])=[N:17][N:18]([CH3:20])[CH:19]=4)[C:5]=3[C:4]=2[CH:3]=1.[CH3:24][S:25]([C:28]1[CH:29]=[C:30](B(O)O)[CH:31]=[CH:32][CH:33]=1)(=[O:27])=[O:26]>>[CH3:20][N:18]1[CH:19]=[C:15]([N:14]2[C:5]3[C:4]4[CH:3]=[C:2]([C:32]5[CH:31]=[CH:30][CH:29]=[C:28]([S:25]([CH3:24])(=[O:27])=[O:26])[CH:33]=5)[CH:11]=[CH:10][C:9]=4[N:8]=[CH:7][C:6]=3[N:12]([CH3:23])[C:13]2=[O:22])[C:16]([CH3:21])=[N:17]1

Participants

3

Reactant 2

HCID 27735423-(Methylsulfonyl)phenylboronic acidHCID 596197398-Bromo-1-(1,3-dimethyl-1H-pyrazol-4-yl)-3-methyl-1,3-dihydro-imidazo[4,5-c]quinolin-2-one2×

Product 1

HCID 596197691-(1,3-Dimethyl-1H-pyrazol-4-yl)-8-(3-methanesulfonyl-phenyl)-3-methyl-1,3-dihydro-imidazo[4,5-c]quinolin-2-one

Procedure

The title compound was synthesized in a similar manner as described for Example 1.1 using 8-bromo-1-(1,3-dimethyl-1H-pyrazol-4-yl)-3-methyl-1,3-dihydro-imidazo[4,5-c]quinolin-2-one (Intermediate A, 40 mg, 0.107 mmol) and (3-methylsulfonylphenyl)boronic acid (Combi-Blocks, San Diego, USA, 26 mg, 0.127 mmol) to give the title compound as a white solid. (HPLC: tR 2.45 min (Method A); M+H=448 MS-ES; 1H-NMR (d6-DMSO, 400 MHz) 9.00 (s, 1H), 8.19-8.11 (m, 2H), 8.02-7.97 (m, 1H), 7.95-7.86 (m, 3H), 7.80-7.74 (m, 1H), 7.64-7.60 (m, 1H), 3.93 (s, 3H), 3.59 (s, 3H), 3.33-3.30 (3H), 1.94 (s, 3H))

Workup

  1. customThe title compound was synthesized in a similar manner

Sources & evidence

ORD record
ord-d38bb44d1e8d43bab3557114a98a151d
Source dataset
uspto-grants-2013_07
Patent number
US08476294B2

Reaction notes

Loading…