2-(Cyclopropylmethoxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine → HCID 49835427, compound

HRID 445589Notes

Reaction equation

HRID 445589 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.[CH:24]1([CH2:27][O:28][C:29]2[N:34]=[CH:33][C:32](B3OC(C)(C)C(C)(C)O3)=[CH:31][CH:30]=2)[CH2:26][CH2:25]1>>[CH:24]1([CH2:27][O:28][C:29]2[N:34]=[CH:33][C:32]([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)=[CH:31][CH:30]=2)[CH2:25][CH2:26]1

Participants

3

Reactant 2

HCID 242087972-(Cyclopropylmethoxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 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 49835427HCID 49835427, 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 6-(cyclopropylmethoxy)pyridine-3-boronic acid pinacol ester (ABCR, Karlsruhe, Germany, 36 mg, 0.131 mmol) to give the title compound as a white solid. (HPLC: tR 2.88 min (Method A); M+H=441 MS-ES; 1H-NMR (d6-DMSO, 400 MHz) 8.95 (s, 1H), 8.29-8.23 (m, 1H), 8.16-8.04 (m, 2H), 7.92-7.85 (m, 1H), 7.80-7.72 (m, 1H), 7.49-7.43 (m, 1H), 6.98-6.90 (m, 1H), 4.15-4.09 (m, 2H), 3.90 (s, 3H), 3.57 (s, 3H), 1.94 (s, 3H), 1.31-1.17 (m, 1H), 0.62-0.48 (m, 2H), 0.40-0.30 (m, 2H))

Workup

  1. customThe title compound was synthesized in a similar manner

Sources & evidence

ORD record
ord-f093db2cd3034545b70a3b2e41a3f4b4
Source dataset
uspto-grants-2013_07
Patent number
US08476294B2

Reaction notes

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