Ammonium formate → HCID 58653659, compound

HRID 1676026Notes

Reaction equation

HRID 1676026 reaction equation
[N:1]1([C:10]([C:17]2[CH:22]=[CH:21][C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:19][CH:18]=2)=[CH:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.C([O-])=O.[NH4+]>C(O)C.O.[Pd]>[N:1]1([CH:10]([C:17]2[CH:18]=[CH:19][C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:21][CH:22]=2)[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 67351563HCID 67351563, compound

Product 1

HCID 58653659HCID 58653659, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of ethyl 3-(1H-benzimidazol-1-yl)-3-(1,1′-biphenyl)-4-yl-2-propenoate (318 mg, 861 μmol) in a mixture of ethanol and water (17:2, 4.2 mL) was added palladium on carbon (47 mg, 10% w/w Pd) and ammonium formate (218 mg, 3.46 mmol). The suspension was brought to reflux for 3 hours, cooled to room temperature, and was filtered through a pad of Celite® and evaporated in vacuo. The residue was purified by flash column chromatography on silica gel, eluting with a mixture of dichloromethane and methanol (97:3) to afford the title compound, [LCMS (Method A, Mobile Phase I) RT=6.51 min, MH+ 371.7].

Workup

  1. temperatureto reflux for 3 hours
  2. filtrationwas filtered through a pad of Celite®
  3. customevaporated in vacuo
  4. customThe residue was purified by flash column chromatography on silica gel
  5. washeluting with a mixture of dichloromethane and methanol (97:3)

Sources & evidence

ORD record
ord-ef1d3b1dc53e43c692ddb776ac274d05
Source dataset
uspto-grants-2011_08
Patent number
US08003806B2

Reaction notes

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