Phenethyl bromide → HCID 66732112, compound

HRID 1037622Notes

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-c088a60b2fd444428b957c31bf8c3d9a
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546564B2

Reaction notes

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