Toluene → HCID 86673036, compound

HRID 1853276Notes

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].P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(B2OC(C)(C)C(C)(C)O2)CC1.[Cl-].[NH4+:49].[C:50]1([CH3:56])[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]([O:5][N:6]=[C:7]1[C:16]2[C:11](=[CH:12][C:13]([C:56]#[C:50][C:51]3[CH:52]=[CH:53][CH:54]=[CH:55][N:49]=3)=[CH:14][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: 120 °C

Procedure

A solution of 6-bromo-2-isoquinolin-3-yl-chromen-4-one O-tert-butyl oxime (100 mg, 0.236 mmol), palladium acetate (3 mg, 0.014 mmol), potassium phosphate (175 mg, 0.826 mmol), dicyclohexylbiphenylphosphine (8 mg, 0.024 mmol), Cyclopropylboronic acid pinacol ester (99 mg, 0.59 mmol) in toluene (3 ml) was degassed with argon for 10 min. The reactor was sealed and heated at 120° C. for 18 hours. The mixture was poured onto a saturated aqueous solution of ammonium chloride, extracted with ethyl acetate, washed with 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-7-(pyridin-2-yl-ethynyl)-chromen-4-one O-tert-butyl oxime (18 mg, 20%).

Workup

customThe reactor was sealed
extractionextracted with ethyl acetate
washwashed with 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-a614c461a5c6435a99c6c660cddfda8a
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962627B2

Reaction notes

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