Ammonium formate → HCID 66712803, compound

HRID 1866299Notes

Reaction equation

HRID 1866299 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][CH:14]=[C:13]([O:19][CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1)[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][CH:14]=[C:13]([O:19][CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1)[CH:12]=2)=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 86595467HCID 86595467, compound

Product 1

HCID 66712803HCID 66712803, compoundYield 72.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 1-bromo-7-cyclohexyloxy-4-hydroxy-isoquinoline-3-carboxylic acid butyl ester (936 mg) in ethyl acetate (25 ml) was added 10% Pd/C (50% wet) (430 mg) and then ammonium formate (1.4 g). Resulting mixture was refluxed for 4 h. After cooling, reaction mixture was filtered and concentrated. The residue was purified by silica gel chromatography (3%-10% ethyl acetate in methylene chloride) to give the title compound (550 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 (3%-10% ethyl acetate in methylene chloride)

Sources & evidence

ORD record
ord-a20115f3577d43749cc4da3ca3e1e2b0
Source dataset
uspto-grants-2009_12
Patent number
US07629357B2

Reaction notes

Loading…