(3-hydroxyphenyl)boronic Acid → HCID 59619642, compound

HRID 445581Notes

Reaction equation

HRID 445581 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.[OH:24][C:25]1[CH:26]=[C:27](B(O)O)[CH:28]=[CH:29][CH:30]=1>>[CH3:20][N:18]1[CH:19]=[C:15]([N:14]2[C:5]3[C:4]4[CH:3]=[C:2]([C:29]5[CH:28]=[CH:27][CH:26]=[C:25]([OH:24])[CH:30]=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 2734359(3-hydroxyphenyl)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 59619642HCID 59619642, compound

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, 39 mg, 0.105 mmol) and 3-hydroxyphenylboronic acid (Aldrich, Buchs, Switzerland, 17 mg, 0.123 mmol) to give the title compound as a white solid. (HPLC: tR 2.46 min (Method A); M+H=386 MS-ES; 1H-NMR (d6-DMSO, 400 MHz) 9.58 (s, 1H), 8.95 (s, 1H), 8.20-8.11 (m, 1H), 8.10-8.01 (m, 1H), 7.88-7.77 (m, 1H), 7.57-7.47 (m, 1H), 7.31-7.20 (m, 1H), 6.93-6.83 (m, 2H), 6.82-6.73 (m, 1H), 3.95 (s, 3H), 3.58 (s, 3H), 1.95 (s, 3H))

Workup

  1. customThe title compound was synthesized in a similar manner

Sources & evidence

ORD record
ord-339ef54f160a4a69ae46980fcc76303c
Source dataset
uspto-grants-2013_07
Patent number
US08476294B2

Reaction notes

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