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

HRID 445598Notes

Reaction equation

HRID 445598 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.[N:24]1([C:29]2[CH:34]=[CH:33][C:32](B(O)O)=[CH:31][CH:30]=2)[CH:28]=[CH:27][CH:26]=[N:25]1>>[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][C:29]([N:24]6[CH:28]=[CH:27][CH:26]=[N:25]6)=[CH:34][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 16640552(4-(1H-Pyrazol-1-yl)phenyl)boronic 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 596200131-(1,3-Dimethyl-1H-pyrazol-4-yl)-3-methyl-8-(4-pyrazol-1-yl-phenyl)-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, 0.106 mmol) and 4-(1H-pyrazol-1-yl)phenylboronic acid (Combi-Blocks, San Diego, USA, 24 mg, 0.126 mmol) to give the title compound as a white solid. (HPLC: tR 2.79 min (Method A); M+H=436 MS-ES; 1H-NMR (d6-DMSO, 400 MHz) 8.96 (s, 1H), 8.60-8.56 (m, 1H), 8.19-8.15 (m, 1H), 8.13-8.07 (m, 1H), 7.99-7.93 (m, 3H), 7.80-7.75 (m, 1H), 7.63-7.56 (m, 3H), 6.59-6.53 (m, 1H), 3.95 (s, 31-1), 3.57 (s, 3H), 1.97 (s, 3H))

Workup

  1. customThe title compound was synthesized in a similar manner

Sources & evidence

ORD record
ord-721da8e5cde540f58927cba256d0e4df
Source dataset
uspto-grants-2013_07
Patent number
US08476294B2

Reaction notes

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