Formic Acid → 2-cyclopropyl-3-(2'-methoxycarbonylbiphenyl-4-yl)methyl-7-methyl-3H-imidazo[4,5-b]pyridine

HRID 743767Notes

Reaction equation

HRID 743767 reaction equation
[CH:1]1([C:4]2[N:14]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[C:28]([O:30][CH3:31])=[O:29])=[CH:18][CH:17]=3)[C:7]3=[N:8][CH:9]=[C:10](Br)[C:11]([CH3:12])=[C:6]3[N:5]=2)[CH2:3][CH2:2]1.C(N(CC)CC)C.C(O)=O>[Pd].C1(C)C=CC=CC=1>[CH:1]1([C:4]2[N:14]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[C:28]([O:30][CH3:31])=[O:29])=[CH:18][CH:17]=3)[C:7]3=[N:8][CH:9]=[CH:10][C:11]([CH3:12])=[C:6]3[N:5]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 284Formic AcidHCID 8471TriethylamineHCID 158372582-cyclopropyl-3-(2'-methoxycarbonylbiphenyl-4-yl)methyl-6-bromo-7-methyl-3H-imidazo[4,5-b]pyridine

Product 1

HCID 110367292-cyclopropyl-3-(2'-methoxycarbonylbiphenyl-4-yl)methyl-7-methyl-3H-imidazo[4,5-b]pyridineYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1140TolueneSolvent

Procedure

Toluene (30 ml) was mixed with 3.0 g (6.3 mmol) of 2-cyclopropyl-3-(2'-methoxycarbonylbiphenyl-4-yl)methyl-6-bromo-7-methyl-3H-imidazo[4,5-b]pyridine, 10% Pd-C (100 mg) and 9.6 g (95 mmol) of triethylamine, followed by the dropwise addition of 2.9 g (63 mmol) of formic acid under stirring. The obtained mixture was heated under reflux for 10 hours. The reaction liquid was brought to room temperature, and filtered to remove the catalyst, and then the filtrate was subjected to vacuum concentration. Chloroform (100 ml) and water (100 ml) were added to the residue and the obtained mixture was caused liquid-liquid separation. The aqueous phase was further extracted with chloroform (50 ml) twice. The organic phases were combined, dried over anhydrous magnesium sulfate and subjected to vacuum concentration. The residue was purified by silica gel column chromatography (a n-hexane/ethyl acetate system) to give 2.3 g of the title compound (yield 92%).

Workup

  1. temperatureThe obtained mixture was heated
  2. temperatureunder reflux for 10 hours
  3. customThe reaction liquid
  4. customwas brought to room temperature
  5. filtrationfiltered
  6. customto remove the catalyst
  7. concentrationthe filtrate was subjected to vacuum concentration
  8. additionChloroform (100 ml) and water (100 ml) were added to the residue
  9. customliquid-liquid separation
  10. extractionThe aqueous phase was further extracted with chloroform (50 ml) twice
  11. dry with materialdried over anhydrous magnesium sulfate
  12. concentrationsubjected to vacuum concentration
  13. customThe residue was purified by silica gel column chromatography (a n-hexane/ethyl acetate system)

Sources & evidence

ORD record
ord-aa8052e94b094f74a784e4c14400f3b6
Source dataset
uspto-grants-1996_09
Patent number
US05557002

Reaction notes

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