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

HRID 913176Notes

Reaction equation

HRID 913176 reaction equation
[CH2:1]([O:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:6]([C:22](O)=[O:23])[C:5]=1[C:25](O)=[O:26])[CH3:2].[NH2:28][C:29]1[CH:34]=[CH:33][C:32]([CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])=[CH:31][C:30]=1[F:41]>CN(C1C=CN=CC=1)C.C(O)(=O)C>[CH2:1]([O:3][C:4]1[C:5]2[C:25](=[O:26])[N:28]([C:29]3[CH:34]=[CH:33][C:32]([CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])=[CH:31][C:30]=3[F:41])[C:22](=[O:23])[C:6]=2[C:7]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=12)[CH3:2]

Participants

5

Reactant 2

HCID 580124801-(Ethyloxy)-4-[(phenylmethyl)oxy]-2,3-naphthalenedicarboxylic acidHCID 59760056Ethyl 2-(4-amino-3-fluorophenyl)acetate

Product 1

HCID 58012495Ethyl (4-{4-(ethyloxy)-1,3-dioxo-9-[(phenylmethyl)oxy]-1,3-dihydro-2H-benzo[f]isoindol-2-yl}-3-fluorophenyl)acetateYield 110.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 1-(ethyloxy)-4-[(phenylmethyl)oxy]-2,3-naphthalenedicarboxylic acid (1.40 g, 3.32 mmol), ethyl (4-amino-3-fluorophenyl)acetate (1.24 g, 6.30 mmol) and DMAP (0.121 g, 0.995 mmol) were heated to 120° C. in acetic acid (20 ml) for 6 hours. The reaction mixture was triturated with water and the resulting yellow solid was collected by filtration and dried in the vacuum oven to give the title compound (1.93 g, 3.66 mmol). LC/MS: Rt=3.95, [MH]+ 528.

Workup

  1. customThe reaction mixture was triturated with water
  2. filtrationthe resulting yellow solid was collected by filtration
  3. customdried in the vacuum oven

Sources & evidence

ORD record
ord-ace76eda108b4092a6d51759b9917686
Source dataset
uspto-grants-2011_09
Patent number
US08026270B2

Reaction notes

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