4-Fluoroiodobenzene → HCID 59375138, compound

HRID 1811038Notes

Reaction equation

HRID 1811038 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][NH:8][C:9]2=[O:12])=[CH:4][CH:3]=1.[F:13][C:14]1[CH:19]=[CH:18][C:17](I)=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.[Cu]I>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][N:8]([C:17]3[CH:18]=[CH:19][C:14]([F:13])=[CH:15][CH:16]=3)[C:9]2=[O:12])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 96054-FluoroiodobenzeneHCID 11430Potassium CarbonateHCID 250673307-Bromo-3,4-dihydroisoquinolin-1(2H)-one2×

Product 1

HCID 59375138HCID 59375138, compoundYield 47.1%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 7-bromo-3,4-dihydroisoquinolin-1(2H)-one (Intermediate 23-1, 60 mg, 0.265 mmol), 1-fluoro-4-iodobenzene (118 mg, 0.531 mmol), potassium carbonate (36.7 mg, 0.265 mmol) and copper (I) iodide (10.11 mg, 0.053 mmol) in DMF (1.000 mL) was heated at 130° C. for 5 h. The mixture was cooled to rt and filtered through a Celite pad, and the solids were washed with EtOAc. The filtrate was washed with water and brine, dried and concentrated. The residue was purified by column chromatography (eluting with a gradient from 90:10 to 60:40 hexane-EtOAc) to give 7-bromo-2-(4-fluorophenyl)-3,4-dihydroisoquinolin-1(2H)-one (40 mg, 47%). 1H NMR (400 MHz, chloroform-d) δ 7.15-7.27 (4 H, m), 7.04-7.13 (2 H, m), 6.48 (1 H, d, J=1.94 Hz), 2.96-3.08 (2 H, m), 2.73-2.84 (2 H, m). Mass spectrum m/z 320, 322 (M+H)+.

Workup

  1. temperatureThe mixture was cooled to rt
  2. filtrationfiltered through a Celite pad
  3. washthe solids were washed with EtOAc
  4. washThe filtrate was washed with water and brine
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography (
  8. washeluting with a gradient from 90:10 to 60:40 hexane-EtOAc)

Sources & evidence

ORD record
ord-4cac099498b14fc79d5b5ac270ed324d
Source dataset
uspto-grants-2013_01
Patent number
US08362065B2

Reaction notes

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