Ethyl (4-{4-(ethyloxy)-1,3-dioxo-9-[(phenylmethyl)oxy]-1,3-dihydro-2H-benzo[f]isoindol-2-yl}-3-fluorophenyl)acetate → Ethyl {4-[4-(ethyloxy)-9-hydroxy-1,3-dioxo-1,3-dihydro-2H-benzo[f]isoindol-2-yl]-3-fluorophenyl}acetate

HRID 913177Notes

Reaction equation

HRID 913177 reaction equation
C([O:3][C:4]1[C:12]2[C:11](=[O:13])[N:10]([C:14]3[CH:19]=[CH:18][C:17]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:16][C:15]=3[F:26])[C:9](=[O:27])[C:8]=2[C:7]([O:28][CH2:29][C:30]2C=CC=CC=2)=[C:6]2[CH:36]=[CH:37][CH:38]=[CH:39][C:5]=12)C>[Pd].C(O)C>[CH2:29]([O:28][C:7]1[C:8]2[C:9](=[O:27])[N:10]([C:14]3[CH:19]=[CH:18][C:17]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:16][C:15]=3[F:26])[C:11](=[O:13])[C:12]=2[C:4]([OH:3])=[C:5]2[CH:39]=[CH:38][CH:37]=[CH:36][C:6]=12)[CH3:30]

Participants

4

Reactant 1

HCID 58012495Ethyl (4-{4-(ethyloxy)-1,3-dioxo-9-[(phenylmethyl)oxy]-1,3-dihydro-2H-benzo[f]isoindol-2-yl}-3-fluorophenyl)acetate

Product 1

HCID 58012505Ethyl {4-[4-(ethyloxy)-9-hydroxy-1,3-dioxo-1,3-dihydro-2H-benzo[f]isoindol-2-yl]-3-fluorophenyl}acetateYield 107.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

10% Palladium on carbon (0.175 g) was suspended in ethanol (150 ml), to this was added ethyl (4-{4-(ethyloxy)-1,3-dioxo-9-[(phenylmethyl)oxy]-1,3-dihydro-2H-benzo[f]isoindol-2-yl}-3-fluorophenyl)acetate (1.75 g, 3.32 mmol). The reaction was stirred at room temperature under an atmosphere of hydrogen for 3 hours. This was filtered through a bed of celite under a blanket of argon, and washed with dichloromethane. The filtrate was evaporated to give a yellow solid (1.56 g, 3.57 mmol). LC/MS: Rt=3.50, [MH]+ 438.

Workup

  1. filtrationThis was filtered through a bed of celite under a blanket of argon
  2. washwashed with dichloromethane
  3. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-eddc7822446041f68c21dc6ac65de503
Source dataset
uspto-grants-2011_09
Patent number
US08026270B2

Reaction notes

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