1,2-Dimethoxyethane → HCID 86673044, compound

HRID 1853277Notes

Reaction equation

[C:1]([O:5][N:6]=[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14](Br)[CH:15]=2)[O:10][C:9]([C:18]2[N:19]=[CH:20][C:21]3[C:26]([CH:27]=2)=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:8]1)([CH3:4])([CH3:3])[CH3:2].CC(C)([O-])C.[K+].[NH:34]1[CH2:38][CH2:37][CH2:36][CH2:35]1.COCCOC>C(OCC)(=O)C>[C:1]([O:5][N:6]=[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([N:34]3[CH2:38][CH2:37][CH2:36][CH2:35]3)[CH:15]=2)[O:10][C:9]([C:18]2[N:19]=[CH:20][C:21]3[C:26]([CH:27]=2)=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:8]1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

A vial was charged with 6-bromo-2-isoquinolin-3-yl-chromen-4-one O-tert-butyl oxime (100 mg, 0.236 mmol), Pd-PEPPSI® (3 mg, 0.005 mmol), potassium tert-butoxide (40 mg, 0.354 mmol) and purged with argon for 15 min. Pyrrolidine (24 μl, 0.283 mmol) and dry 1,2-dimethoxyethane (1 ml) were added and the solution was heated at 80° C. for 18 hours. The mixture was diluted with ethyl acetate washed with a saturated aqueous solution of ammonium chloride, water and brine, dried over sodium sulfate and purified by flash chromatography over silica gel (cyclohexane/dichloromethane: 0-80%) to yield 2-isoquinolin-3-yl-6-(pyrrolidin-1-yl)-chromen-4-one O-tert-butyl oxime (64 mg, 65%).

Workup

custompurged with argon for 15 min
washwashed with a saturated aqueous solution of ammonium chloride, water and brine
dry with materialdried over sodium sulfate
custompurified by flash chromatography over silica gel (cyclohexane/dichloromethane: 0-80%)

Sources & evidence

ORD record: ord-cc70a52e1fd64056bd5021c0cb5bbc7c
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962627B2

Reaction notes

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