4-Fluorobenzyl bromide → HCID 117771288, compound

HRID 2201587Notes

Reaction equation

HRID 2201587 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][NH:8][C:9]2=[O:12])=[CH:4][CH:3]=1.Br[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1.CC(C)([O-])C.[K+]>C1COCC1.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][N:8]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)[C:9]2=[O:12])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 680214-Fluorobenzyl bromideHCID 112761337-Bromoisoquinolin-1-olHCID 23665647Potassium tert-butoxide

Product 1

HCID 117771288HCID 117771288, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 7-bromoisoquinolin-1(2H)-one (300 mg, 1.34 mmol) and 1-(bromomethyl)-4-fluorobenzene (380 mg, 2.01 mmol) in THF (8 ml) was added potassium t-butoxide (300 mg, 2.68 mmol) and tetrabutylammonium iodide (50 mg, 0.13 mmol). The resulting mixture was stirred at RT for 3 h. The solid was removed by filtration, then concentrated in vacuo. The resulting residue was purified using column chromatography (eluted with 0-30% EtOAc/DCM) to provide 7-bromo-2-(4-fluorobenzyl)-3,4-dihydroisoquinolin-1(2H)-one (410 mg, yield: 92%) (M+H)+: 333.

Workup

  1. customThe solid was removed by filtration
  2. concentrationconcentrated in vacuo
  3. customThe resulting residue was purified
  4. washcolumn chromatography (eluted with 0-30% EtOAc/DCM)

Sources & evidence

ORD record
ord-179e1ba2ac974377a95e8afde2118d88
Source dataset
uspto-grants-2016_06
Patent number
US09364482B2

Reaction notes

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