(2,2-Difluoro-1,3-dioxaindan-4-yl)boronic acid → 8-(2,2-Difluoro-benzo[1,3]dioxol-4-yl)-1-(1,3-dimethyl-1H-pyrazol-4-yl)-3-methyl-1,3-dihydro-imidazo[4,5-c]quinolin-2-one

HRID 445584Notes

Reaction equation

HRID 445584 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.[F:24][C:25]1([F:37])[O:29][C:28]2[CH:30]=[CH:31][CH:32]=[C:33](B(O)O)[C:27]=2[O:26]1>>[F:37][C:25]1([F:24])[O:26][C:27]2[CH:33]=[CH:32][CH:31]=[C:30]([C:2]3[CH:11]=[CH:10][C:9]4[N:8]=[CH:7][C:6]5[N:12]([CH3:23])[C:13](=[O:22])[N:14]([C:15]6[C:16]([CH3:21])=[N:17][N:18]([CH3:20])[CH:19]=6)[C:5]=5[C:4]=4[CH:3]=3)[C:28]=2[O:29]1

Participants

3

Reactant 2

HCID 16427145(2,2-Difluoro-1,3-dioxaindan-4-yl)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 498353738-(2,2-Difluoro-benzo[1,3]dioxol-4-yl)-1-(1,3-dimethyl-1H-pyrazol-4-yl)-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 2,2-difluorobenzo[1,3]dioxole-4-boronic acid (Apollo, Cheshire, United Kingdom, 26 mg, 0.130 mmol) to give the title compound as a white solid. (HPLC: tR 2.95 min (Method A); M+H=450 MS-ES; 1H-NMR (d6-DMSO, 400 MHz) 9.01 (s, 1H), 8.18-8.13 (m, 1H), 8.08 (s, 1H), 7.97-7.91 (m, 1H), 7.88-7.84 (m, 1H), 7.441-7.38 (m, 2H), 7.36-7.29 (m, 1H), 3.85 (s, 3H), 3.58 (s, 3H), 1.94 (s, 3H))

Workup

  1. customThe title compound was synthesized in a similar manner

Sources & evidence

ORD record
ord-d2de488e609c4104ac6dbbd3891c3f7e
Source dataset
uspto-grants-2013_07
Patent number
US08476294B2

Reaction notes

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