Water → N-acetyl-N-(4-bromoisoquinolin-1-yl)acetamide

HRID 1945733Notes

Reaction equation

[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([NH2:12])=[N:4][CH:3]=1.C(N([CH2:20][CH3:21])C(C)C)(C)C.[C:22](Cl)(=[O:24])[CH3:23].[OH2:26]>C(Cl)Cl>[C:22]([N:12]([C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]([Br:1])=[CH:3][N:4]=1)[C:20](=[O:26])[CH3:21])(=[O:24])[CH3:23]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 4-bromoisoquinolin-1-amine (403 mg, 1.81 mmol) in methylene chloride (11 mL) at 0° C. was added N,N-diisopropylethylamine (1.57 mL, 9.03 mmol), followed by acetyl chloride (0.321 mL, 4.52 mmol) dropwise. The mixture was stirred at 0° C. for 10 min then at room temperature for 2 h. The mixture was diluted with DCM (10 mL). Water (20 mL) was added. The organic layer was separated. The aqueous solution was extracted with DCM (10 mL). The combined DCM solutions were dried (Na2SO4). After filtration and concentration, the crude was purified with flash chromatography to give the desired product (470 mg, 85%). 1H NMR (400 MHz, DMSO) δ 8.79 (s, 1H), 8.23 (d, J=8.4, 1H), 8.13 (d, J=8.4, 1H), 8.05 (t, J=7.7, 1H), 7.87 (t, J=7.6, 1H), 2.23 (s, 6H).

Workup

waitat room temperature for 2 h
customThe organic layer was separated
extractionThe aqueous solution was extracted with DCM (10 mL)
dry with materialThe combined DCM solutions were dried (Na2SO4)
filtrationAfter filtration and concentration
customthe crude was purified with flash chromatography

Sources & evidence

ORD record: ord-8e3632cf7e26456b9feb01e7b1d6240d
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08394796B2

Reaction notes

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