Tricyclohexylphosphine → HCID 67959129, compound

HRID 1404957Notes

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.[CH:19]1(B(O)O)[CH2:21][CH2:20]1.CC(C)([O-])C.[K+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.C1(C)C=CC=CC=1>[CH:19]1([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)[CH2:21][CH2:20]1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of tert-butyl 8-bromo-2,3-dihydrothieno[2,3-f][1,4]oxazepine-4(5H)-carboxylate (16.0 g) obtained in Example 1, steps 1-3, cyclopropylboronic acid (8.23 g), potassium tert-butoxide (12.5 g), tricyclohexylphosphine (1.88 g), palladium acetate (754 mg) and toluene (400 mL) was stirred at 100° C. for 8 hr, the reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (solvent gradient; 0→10% ethyl acetate/hexane) to give the title compound (10.6 g, 75.1%) as an oil.

Workup

extractionthe mixture was extracted with ethyl acetate
dry with materialThe extract was dried over anhydrous magnesium sulfate
customthe solvent was evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (solvent gradient; 0→10% ethyl acetate/hexane)

Sources & evidence

ORD record: ord-b2fc76ea39c943b5a3ff48df597f009d
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08916549B2

Reaction notes

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