1,2-Dimethoxyethane → 4-(6-Chloro-4-methyl-pyridin-3-yl)-5-methoxy-10-oxa-tricyclo[5.2.1.02,6]dec-4-en-3-one

HRID 41685

Reaction equation

I[C:2]1[C:3](=[O:14])[CH:4]2[CH:9]([C:10]=1[O:11][CH3:12])[CH:8]1[O:13][CH:5]2[CH2:6][CH2:7]1.[Cl:15][C:16]1[N:21]=[CH:20][C:19](B(O)O)=[C:18]([CH3:25])[CH:17]=1.COCCOC.C(=O)([O-])[O-].[Na+].[Na+]>Cl.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:15][C:16]1[N:21]=[CH:20][C:19]([C:2]2[C:3](=[O:14])[CH:4]3[CH:9]([C:10]=2[O:11][CH3:12])[CH:8]2[O:13][CH:5]3[CH2:6][CH2:7]2)=[C:18]([CH3:25])[CH:17]=1

Participants

Conditions

Temperature: 130 °C

Procedure

A microwave vial is charged with 4-iodo-5-methoxy-10-oxa-tricyclo[5.2.1.0*2,6*]dec-4-en-3-one (184 mg, 0.6 mmol), 6-chloro-4-methylpyridine-3-boronic acid (103 mg, 0.6 mmol) and bis(triphenylphosphine)palladium dichloride (21 mg, 0.03 mmol). DME (1 ml) is added, followed by 2N aqueous sodium carbonate solution (0.6 ml, 1.2 mmol) and the reaction is heated to 130° C. by microwave irradiation, with stirring, for 30 minutes. The reaction is then diluted with 2N HCl (20 ml), extracted with ethyl acetate (20 ml), and the organic layer is removed and purified by flash chromatography on silica gel to give 4-(6-chloro-4-methyl-pyridin-3-yl)-5-methoxy-10-oxa-tricyclo[5.2.1.0*2,6*]dec-4-en-3-one (119 mg).

Workup

extractionextracted with ethyl acetate (20 ml)
customthe organic layer is removed
custompurified by flash chromatography on silica gel

Sources & evidence

ORD record: ord-7aaa8d583ecf4c4fbab7dc484af1bd7e
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08530667B2

Linked notes

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