Cesium fluoride → HCID 86673032, compound

HRID 1853264Notes

Reaction equation

[C:1]([O:5][N:6]=[C:7]1[C:16]2[C:11](=[CH:12][C:13](Br)=[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].[F-].[Cs+].[CH:30](/B(O)O)=[CH:31]\[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>COCCOC.CO.ClCCl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]([O:5][N:6]=[C:7]1[C:16]2[C:11](=[CH:12][C:13](/[CH:30]=[CH:31]/[C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=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: 150 °C

Procedure

In a microwave vial, a solution of 7-bromo-2-isoquinolin-3-yl-chromen-4-one O-tert-butyl oxime (200 mg, 0.47 mmol), cesium fluoride (213 mg, 1.41 mmol) and trans-styryl boronic acid (160 mg, 1.07 mmol) in 1,2-dimethoxyethane (3.2 ml) and methanol (1.6 ml) was degassed with argon for 20 min and then tetrakis(triphenylphosphine)palladium (30 mg, 0.026 mmol) was added. The vial was sealed and the mixture was heated under microwave irradiation to 150° C. for 5 min. After cooling, the solution was diluted with dichloromethane and absorbed over silica gel for purification by flash chromatography (gradient cyclohexane/dichloromethane: 0-80%) to yield 2-Isoquinolin-3-yl-7-((E)-styryl)-chromen-4-one O-tert-butyl oxime (160 mg, 76%) as a yellow solid.

Workup

customThe vial was sealed
temperatureAfter cooling
customabsorbed over silica gel for purification by flash chromatography (gradient cyclohexane/dichloromethane: 0-80%)

Sources & evidence

ORD record: ord-e64d892cefb74a4eac05263a9413e8f6
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962627B2

Reaction notes

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