(6-Methoxypyridin-3-yl)boronic acid → 1-[1-(2-Hydroxy-ethyl)-3-methyl-1H-pyrazol-4-yl]-8-(6-methoxy-pyridin-3-yl)-3-methyl-1,3-dihydro-imidazo[4,5-c]quinolin-2-one

HRID 445664Notes

Reaction equation

HRID 445664 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[N:12]([CH3:25])[C:13](=[O:24])[N:14]([C:15]4[C:16]([CH3:23])=[N:17][N:18]([CH2:20][CH2:21][OH:22])[CH:19]=4)[C:5]=3[C:4]=2[CH:3]=1.[CH3:26][O:27][C:28]1[CH:33]=[CH:32][C:31](B(O)O)=[CH:30][N:29]=1>>[OH:22][CH2:21][CH2:20][N:18]1[CH:19]=[C:15]([N:14]2[C:5]3[C:4]4[CH:3]=[C:2]([C:31]5[CH:30]=[N:29][C:28]([O:27][CH3:26])=[CH:33][CH:32]=5)[CH:11]=[CH:10][C:9]=4[N:8]=[CH:7][C:6]=3[N:12]([CH3:25])[C:13]2=[O:24])[C:16]([CH3:23])=[N:17]1

Participants

3

Reactant 2

HCID 2734368(6-Methoxypyridin-3-yl)boronic acidHCID 596199998-bromo-1-[1-(2-hydroxy-ethyl)-3-methyl-1H-pyrazol-4-yl]-3-methyl-1,3-dihydro-imidazo[4,5-c]quinolin-2-one

Product 1

HCID 498356681-[1-(2-Hydroxy-ethyl)-3-methyl-1H-pyrazol-4-yl]-8-(6-methoxy-pyridin-3-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-(2-hydroxy-ethyl)-3-methyl-1H-pyrazol-4-yl]-3-methyl-1,3-dihydro-imidazo[4,5-c]quinolin-2-one (Stage 103.1.1, 37.4 mg, 0.093 mmol) and 2-methoxypyridine-5-boronic acid (Aldrich, Buchs, Switzerland, 20 mg, 0.131 mmol) to give the title compound as a white solid. (HPLC: tR 2.42 min (Method A); M+H=431 MS-ES; 1H-NMR (d6-DMSO, 400 MHz) 8.95 (s, 1H), 8.35 (s, 1H), 8.13 (s, 1H), 8.10-8.05 (m, 1H), 7.95-7.88 (m, 1H), 7.81-7.75 (m, 1H), 7.51-7.46 (m, 1H), 6.93-6.86 (m, 1H), 5.00-4.94 (m, 1H), 4.24-4.17 (m, 2H), 3.88 (s, 3H), 3.86-3.74 (m, 2H), 3.57 (s, 3H), 1.94 (s, 3H))

Workup

  1. customThe title compound was synthesized in a similar manner

Sources & evidence

ORD record
ord-aa2358008526440d8625c905b4ff8239
Source dataset
uspto-grants-2013_07
Patent number
US08476294B2

Reaction notes

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