Phenylboronic Acid → HCID 49835423, compound

HRID 445586Notes

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.[C:24]1(B(O)O)[CH:29]=[CH:28][CH:27]=[CH:26][CH: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:24]5[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=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

Reactant 2

HCID 66827Phenylboronic Acid

HCID 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 49835423HCID 49835423, 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, 40 mg, 0.107 mmol) and phenylboronic acid (Aldrich, Buchs, Switzerland, 16.5 mg, 0.135 mmol) to give the title compound as a white solid. (HPLC: tR 2.70 min (Method A); M+H=370 MS-ES; 1H-NMR (d6-DMSO, 400 MHz) 8.95 (s, 1H), 8.16 (s, 1H), 8.11-8.06 (m, 1H), 7.93-7.88 (m, 1H), 7.56-7.53 (m, 1H), 7.50-7.44 (m, 4H), 7.42-7.34 (m, 1H), 3.92 (s, 3H), 3.57 (s, 3H), 1.95 (s, 3H))

Workup

customThe title compound was synthesized in a similar manner

Sources & evidence

ORD record: ord-c34ab62588934a53893ed1eeb9993866
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08476294B2

Reaction notes

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