Phenethyl bromide → HCID 66732542, compound

HRID 1037623Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([OH:12])=[N:7][CH2:6][CH2:5]2.[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:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:6][CH2:5]2

Participants

Conditions

Temperature: 70 °C

Procedure

6-Bromo-1-hydroxy-3,4-dihydroisoquinoline (300 mg, 1.33 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 70° C. After heating for 14 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 residue using flash silica gel chromatography (gradient of 3→18% ethyl acetate/hexanes) provided 6-bromo-2-phenethyl-3,4-dihydroisoquinolin-1-one (201 mg, 0.61 mmol, 46%) as a white solid. This isoquinolinone (201 mg, 0.61 mmol) was converted, via Methods 1 and 2, to compound 12 (90 mg, 50%) which was isolated as a white solid. Activity: A

Workup

temperatureAfter heating for 14 hours
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 residue

Sources & evidence

ORD record: ord-22105d18a3b1492d9e179a05d70b0ed7
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546564B2

Reaction notes

Loading…