[7-Fluoro-2-(4-nitro-phenyl)-1-oxo-1,2-dihydro-isoquinolin-6-yl]-methyl-carbamic acid tert-butyl ester → [2-(4-Amino-phenyl)-7-fluoro-1-oxo-1,2-dihydro-isoquinolin-6-yl]-methyl-carbamic acid tert-butyl ester

HRID 1593046Notes

Reaction equation

HRID 1593046 reaction equation
[C:1]([O:5][C:6](=[O:30])[N:7]([C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][C:18]=1[F:19])[C:15](=[O:20])[N:14]([C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-])=O)=[CH:23][CH:22]=1)[CH:13]=[CH:12]2)[CH3:8])([CH3:4])([CH3:3])[CH3:2]>C(OCC)(=O)C.C(O)C.[Pd]>[C:1]([O:5][C:6](=[O:30])[N:7]([C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][C:18]=1[F:19])[C:15](=[O:20])[N:14]([C:21]1[CH:22]=[CH:23][C:24]([NH2:27])=[CH:25][CH:26]=1)[CH:13]=[CH:12]2)[CH3:8])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 1

HCID 58998426[7-Fluoro-2-(4-nitro-phenyl)-1-oxo-1,2-dihydro-isoquinolin-6-yl]-methyl-carbamic acid tert-butyl ester

Product 1

HCID 58998471[2-(4-Amino-phenyl)-7-fluoro-1-oxo-1,2-dihydro-isoquinolin-6-yl]-methyl-carbamic acid tert-butyl esterYield 92.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of [7-Fluoro-2-(4-nitro-phenyl)-1-oxo-1,2-dihydro-isoquinolin-6-yl]-methyl-carbamic acid tert-butyl ester (0.33 g, 0.79 mmol) in ethyl acetate (6 mL) and ethanol (2 mL) under Ar was added 10% Pd/C (0.13 g, 0.12 mmol Pd). The mixture was hydrogenated under 1 atm H2 for 2 hr, filtered through Celite and concentrated to give 0.28 g (92%) of [2-(4-Amino-phenyl)-7-fluoro-1-oxo-1,2-dihydro-isoquinolin-6-yl]-methyl-carbamic acid tert-butyl ester. RP-HPLC: 3.83 min; ES-MS (M+H)+=384.0; 1H-NMR (DMSO-d6) δ (ppm): 1.32 (s, 9), 3.17 (s, 3), 5.31 (br s, 2), 6.60 (m, 3), 7.00 (d, 2), 7.32 (d, 2), 7.75 (d, 1), 7.86 (d, 1).

Workup

  1. filtrationfiltered through Celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-b8fbd9a753874b9690f8bfaea77047c5
Source dataset
uspto-grants-2007_11
Patent number
US07294635B2

Reaction notes

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