Ammonium formate → HCID 66713014, compound

HRID 250489Notes

Reaction equation

HRID 250489 reaction equation
[CH2:1]([O:5][C:6]([C:8]1[N:9]=[C:10](Br)[C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][C:14]([O:19][CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1)=[CH:13][CH:12]=2)=[O:7])[CH2:2][CH2:3][CH3:4].C([O-])=O.[NH4+]>C(OCC)(=O)C.[Pd]>[CH2:1]([O:5][C:6]([C:8]1[N:9]=[CH:10][C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][C:14]([O:19][CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1)=[CH:13][CH:12]=2)=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 86595482HCID 86595482, compound

Product 1

HCID 66713014HCID 66713014, compoundYield 78.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 1-bromo-6-cyclohexyloxy-4-hydroxy-isoquinoline-3-carboxylic acid butyl ester (1.0 g) in ethyl acetate (20 ml) was added 10% Pd/C (50% wet) (460 mg) and then ammonium formate (1.5 g). Resulting mixture was refluxed for 4 h. After cooling, reaction mixture was filtered and concentrated. The residue was purified by silica gel chromatography (5%-10% ethyl acetate in methylene chloride) to give the title compound (640 mg). MS-(+)-ion M+1=344.22.

Workup

  1. customResulting mixture
  2. temperaturewas refluxed for 4 h
  3. temperatureAfter cooling
  4. customreaction mixture
  5. filtrationwas filtered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography (5%-10% ethyl acetate in methylene chloride)

Sources & evidence

ORD record
ord-0f7aabc436f64e4da8d9cbbd5c7094d6
Source dataset
uspto-grants-2011_01
Patent number
US07863292B2

Reaction notes

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