1(3H)-Isobenzofuranone, 3-bromo- → 1-Ethyl-1,3,4,9-tetrahydro-7-(trifluoromethoxy)pyrano[3,4-b]indole-1-acetic Acid 3-Oxo-1-isobenzofuranyl Ester

HRID 1087954Notes

Reaction equation

HRID 1087954 reaction equation
[CH2:1]([C:3]1([CH2:21][C:22]([OH:24])=[O:23])[C:8]2[NH:9][C:10]3[C:15]([C:7]=2[CH2:6][CH2:5][O:4]1)=[CH:14][CH:13]=[C:12]([O:16][C:17]([F:20])([F:19])[F:18])[CH:11]=3)[CH3:2].Br[CH:26]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:28](=[O:29])[O:27]1>C1COCC1>[O:29]=[C:28]1[C:30]2[C:35](=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:26]([O:23][C:22](=[O:24])[CH2:21][C:3]2([CH2:1][CH3:2])[C:8]3[NH:9][C:10]4[C:15]([C:7]=3[CH2:6][CH2:5][O:4]2)=[CH:14][CH:13]=[C:12]([O:16][C:17]([F:18])([F:20])[F:19])[CH:11]=4)[O:27]1

Participants

4

Reactant 2

HCID 962181(3H)-Isobenzofuranone, 3-bromo-HCID 157030331-Ethyl-1,3,4,9-tetrahydro-7-(trifluoromethoxy)pyrano[3,4-b]indole-1-acetic acid

Product 1

HCID 679008311-Ethyl-1,3,4,9-tetrahydro-7-(trifluoromethoxy)pyrano[3,4-b]indole-1-acetic Acid 3-Oxo-1-isobenzofuranyl EsterYield 74.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-ethyl-1,3,4,9-tetrahydro-7-(trifluoromethoxy)pyrano[3,4-b]indole-1-acetic acid (0.650 g, 1.89 mmol, prepared according to the procedure of Example 1), 3-bromophthalid (0.402 g, 1.89 mmol) and TEA (0.382 g, 3.79 mmol) in dry THF (60 mL) was refluxed for 4 hours. The solvent was evaporated and the residue was partitioned between water and ether. The extracts were washed with 5% NaHCO3 and brine, dried (MgSO4) and evaporated to dryness. Flash chromatography of the residue (on silica Merck-60, eluant: CHCl3) provided 0.670 g (74.6%) of the pure product (as a mixture of diastereomers) which was recrystallized from ether-hexane, m.p. 150° C. (softening starts at 124° C.).

Workup

  1. temperaturewas refluxed for 4 hours
  2. customThe solvent was evaporated
  3. customthe residue was partitioned between water and ether
  4. washThe extracts were washed with 5% NaHCO3 and brine
  5. dry with materialdried (MgSO4)
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-dbba3bae9b5f4002bbc660e056ec72c6
Source dataset
uspto-grants-1990_10
Patent number
US04960902

Reaction notes

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