Phenethyl bromide → HCID 66732112, compound

HRID 2403058Notes

Reaction equation

[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]=[C:9]2[OH:12])=[CH:4][CH:3]=1.[CH2:13](Br)[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[OH-].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1.CC(OC)(C)C>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]([CH2:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:9]2=[O:12])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

7-Bromo-1-hydroxyisoquinoline (300 mg, 1.34 mmol, 1.0 equiv), tetrabutylammonium bromide (50 mg, 0.13 mmol, 0.10 equiv), and phenethyl bromide (220 uL, 1.6 mmol, 1.2 equiv) were combined in toluene (14 mL) and treated with 50% aq. NaOH (3 mL), and the resulting mixture stirred rapidly while heating to 80° C. After 1.5 hours, the mixture was diluted with MTBE and washed with water, saturated NaHCO3, and brine. The organic phase was dried over Na2SO4. Addition of silica gel, concentration, and purification of the crude residue using flash silica gel chromatography (gradient of 2-30% ethyl acetates/hexanes) provided 7-bromo-2-phenethyl-isoquinolin-1-one (340 mg, 1.04 mmol, 77%) as a white solid. This isoquinolinone (340 mg, 1.04 mmol) was converted, via Methods 1 and 2, to compound 11 (141 mg, 46%) which was isolated as a white solid. Activity: B

Workup

washwashed with water, saturated NaHCO3, and brine
dry with materialThe organic phase was dried over Na2SO4
additionAddition of silica gel, concentration, and purification of the crude residue

Sources & evidence

ORD record: ord-bb49b3b356904193a7f0ebad61b34b12
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08802064B2

Reaction notes

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