Water → HCID 21525404, compound

HRID 1638896Notes

Reaction equation

HRID 1638896 reaction equation
NC1C=C([N:10]2[C:18](=[O:19])[C:17]3[CH2:16][CH2:15][CH2:14][CH2:13][C:12]=3[C:11]2=[O:20])C(F)=CC=1Br.BrCC(OCC)=O.C(N(CC)CC)C.O>O1CCOCC1.C1(C)C=CC=CC=1>[C:11]1(=[O:20])[C:12]2[CH:17]([CH2:16][CH2:15][CH2:14][CH:13]=2)[C:18](=[O:19])[NH:10]1

Participants

7

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 8471TriethylamineHCID 15590181HCID 15590181, compound

Product 1

HCID 21525404HCID 21525404, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 312751,4-DioxaneSolvent

Procedure

2-(3-Amino-4-bromo-6-fluorophenyl)-4,5,6,7-tetrahydro-2H-isoindole-1,3-dione (0.85 g) was dissolved in 1,4-dioxane (5 ml), and ethyl bromoacetate (3.3 g) was added thereto. The resultant mixture was refluxed for 6 hours. Triethylamine (0.2 g) was added thereto, and the mixture was refluxed for 1 hour. After being allowed to cool, water and toluene were added to the mixture, which was then extracted with toluene. The toluene layer was dried and concentrated. The residue was purified by silica gel column chromatography to give 1.0 g of 2-(4-bromo-2-fluoro-5-ethoxycarbonylmethylaminophenyl)-4,5,6,7-(tetrahydro-2H-isoindole-1,3-dione (Compound No. 89). nD26.0 1.5281.

Workup

  1. temperaturethe mixture was refluxed for 1 hour
  2. temperatureto cool
  3. extractionwas then extracted with toluene
  4. dry with materialThe toluene layer was dried
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-fafcfbfb3ad44d4bb66e73b4b3d6834e
Source dataset
uspto-grants-1989_11
Patent number
US04881970

Reaction notes

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