Thiophenol → 1-cyclopropyl-3-((3-isopentyl-3H-imidazo[4,5-b]pyridin-2-yl)methyl)-1H-imidazo[4,5-c]pyridin-2(3H)-one

HRID 632857Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[N:10]=[C:9]([CH2:11][N:12]3[C:16]4[CH:17]=[N:18][CH:19]=[CH:20][C:15]=4[N:14]([CH:21]4[CH2:23][CH2:22]4)[C:13]3=[O:24])[N:8]([CH2:25][CH2:26][CH:27]([CH3:29])[CH3:28])[C:5]2=[N:6][CH:7]=1.C([O-])(=O)C.[K+].C1(S)C=CC=CC=1>CO.[Pd]>[CH:21]1([N:14]2[C:15]3[CH:20]=[CH:19][N:18]=[CH:17][C:16]=3[N:12]([CH2:11][C:9]3[N:8]([CH2:25][CH2:26][CH:27]([CH3:28])[CH3:29])[C:5]4=[N:6][CH:7]=[CH:2][CH:3]=[C:4]4[N:10]=3)[C:13]2=[O:24])[CH2:22][CH2:23]1

Participants

Conditions

Temperature: 25 °C

Procedure

To intermediate 16 (0.49 g, 1.09 mmol) in methanol (30 mL) were added potassium acetate (0.128 g, 1.3 mmol), thiophenol (0.5 mL) and wet 10% Pd/C (0.2 g). The reaction mixture was stirred at 25° C. under hydrogen atmosphere. After uptake of H2 (1 eq), the catalyst was filtered off and the filtrate was evaporated. The residue was dissolved in water and dichloromethane. The resulting mixture was successively extracted with dichloromethane dried over MgSO4 and concentrated. The residue was purified by column chromatography using dichloromethane/ methanol. The title compound 24 was collected as a white powder (333 mg, 81%). m/z=377 (M+H)+.

Workup

filtrationAfter uptake of H2 (1 eq), the catalyst was filtered off
customthe filtrate was evaporated
dissolutionThe residue was dissolved in water
extractionThe resulting mixture was successively extracted with dichloromethane
dry with materialdried over MgSO4
concentrationconcentrated
customThe residue was purified by column chromatography
customThe title compound 24 was collected as a white powder (333 mg, 81%)

Sources & evidence

ORD record: ord-52559a17e9c2471b860491300bb56b40
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321767B2

Reaction notes

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