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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 1424488
Notes
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Reaction equation

HRID 1424488 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 7969ThiophenolHCID 517044Potassium AcetateHCID 679917843-((6-bromo-3-isopentyl-3H-imidazo[4,5-b]pyridin-2-yl)methyl)-1-cyclopropyl-1H-imidazo[4,5-c]pyridin-2(3H)-one

Product 1

HCID 573788801-cyclopropyl-3-((3-isopentyl-3H-imidazo[4,5-b]pyridin-2-yl)methyl)-1H-imidazo[4,5-c]pyridin-2(3H)-one

Reagents, catalysts & solvents 2

HCID 23938
Palladium
Catalyst
HCID 887MethanolSolvent

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

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

Sources & evidence

ORD record
ord-a006d4b9e61a4e7d951db1d247a27c1f
Source dataset
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08927720B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes