Ethanol → HCID 67958968, compound

HRID 1404954Notes

Reaction equation

Br[C:2]1[C:11]2[O:10][CH2:9][CH2:8][N:7]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:6][C:5]=2[S:4][CH:3]=1.[O:19]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20]1.CCO.C(=O)([O-])[O-].[Na+].[Na+]>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.O.C1(C)C=CC=CC=1>[O:19]1[CH:23]=[CH:22][C:21]([C:2]2[C:11]3[O:10][CH2:9][CH2:8][N:7]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:6][C:5]=3[S:4][CH:3]=2)=[CH:20]1

Participants

Conditions

Temperature: 95 °C

Procedure

A mixture of tert-butyl 8-bromo-2,3-dihydrothieno[2,3-f][1,4]oxazepine-4(5H)-carboxylate (60.0 mg), 3-furanboronic acid (26.1 mg), EtOH (0.1 ml), 2N aqueous sodium carbonate solution (1 mL), tetrakis(triphenylphosphine)palladium (25 mg) and toluene (2 mL) was stirred at 95° C. for 12 hr under a nitrogen atmosphere, and the reaction mixture was poured into water. The mixture was extracted with ethyl acetate and the extract was washed with water, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (solvent gradient; 0→33% ethyl acetate/hexane) to give the title compound (51.0 mg, 88.1%) as an oil.

Workup

extractionThe mixture was extracted with ethyl acetate
washthe extract was washed with water
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was evaporated under reduced pressure
customthe residue was purified by silica gel column chromatography (solvent gradient; 0→33% ethyl acetate/hexane)

Sources & evidence

ORD record: ord-bfd51f7f1d9c4a7cb82e475fcefac598
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08916549B2

Reaction notes

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