Water → HCID 90178620, compound

HRID 2206207Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][S:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH3:14][C:15]1([CH3:22])[C:19]([CH3:21])([CH3:20])[O:18][BH:17][O:16]1.C(N(CC)CC)C.O>O1CCOCC1.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>[CH3:14][C:15]1([CH3:22])[C:19]([CH3:21])([CH3:20])[O:18][B:17]([C:2]2[CH:7]=[CH:6][C:5]([N:8]3[CH2:13][CH2:12][S:11][CH2:10][CH2:9]3)=[CH:4][CH:3]=2)[O:16]1

Participants

Conditions

Temperature: 100 °C

Procedure

To a mixture of 4-(4-bromophenyl)thiomorpholine (0.40 g), 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.40 g) and triethylamine (0.65 mL) in 1,4-dioxane (15 mL) was added dichlorobis(triphenylphosphine)palladium(II) (0.054 g) under argon atmosphere. The reaction mixture was stirred at 100° C. for 16 hr. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (0.40 g).

Workup

extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record: ord-f322b440797443a88c76c9f5472ef2e8
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09371320B2

Reaction notes

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