4-Fluoroaniline → HCID 118558142, compound

HRID 927271Notes

Reaction equation

HRID 927271 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[Br:9][C:10]1[CH:19]=[CH:18][C:13]([C:14](OC)=[O:15])=[C:12]([CH2:20][C:21](=O)[CH2:22][CH2:23][CH2:24][CH2:25][C:26]([O:28][CH3:29])=[O:27])[CH:11]=1>C(O)(=O)C>[Br:9][C:10]1[CH:11]=[C:12]2[C:13](=[CH:18][CH:19]=1)[C:14](=[O:15])[N:6]([C:5]1[CH:7]=[CH:8][C:2]([F:1])=[CH:3][CH:4]=1)[C:21]([CH2:22][CH2:23][CH2:24][CH2:25][C:26]([O:28][CH3:29])=[O:27])=[CH:20]2

Participants

4

Reactant 2

HCID 97314-FluoroanilineHCID 90094612HCID 90094612, compound

Product 1

HCID 118558142HCID 118558142, compoundYield 50.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

4-Fluoroaniline (98 mg, 0.884 mmol, 1.0 equiv.) was added to a stirred mixture of methyl 4-bromo-2-(7-methoxy-2,7-dioxoheptyl)benzoate (328 mg, 0.884 mmol) in acetic acid (1 mL) and the mixture was stirred at 100° C. for 90 min. After cooling to room temperature, the excess solvent was concentrated, diluted with water and extracted with EtOAc (2×5 mL). The organic layer was dried over Na2SO4, filtered and evaporated to dryness. The residue was purified by column chromatography on silica gel eluting with 0-10% EtOAc/hexanes to give 193 mg of methyl 5-(6-bromo-2-(4-fluorophenyl)-1-oxo-1,2-dihydroisoquinolin-3-yl)pentanoate as a yellow oil.

Workup

  1. temperatureAfter cooling to room temperature
  2. concentrationthe excess solvent was concentrated
  3. additiondiluted with water
  4. extractionextracted with EtOAc (2×5 mL)
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customThe residue was purified by column chromatography on silica gel eluting with 0-10% EtOAc/hexanes

Sources & evidence

ORD record
ord-947cc9cffbd9459195ac5a877dffc021
Source dataset
uspto-grants-2016_03
Patent number
US09290454B2

Reaction notes

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