Water → HCID 131735842, compound

HRID 2206211Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][C@@H:9]2[CH3:14])=[CH:4][CH:3]=1.[CH3:15][C:16]1([CH3:23])[C:20]([CH3:22])([CH3:21])[O:19][BH:18][O:17]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@H:9]1[CH2:10][O:11][CH2:12][CH2:13][N:8]1[C:5]1[CH:6]=[CH:7][C:2]([B:18]2[O:19][C:20]([CH3:22])([CH3:21])[C:16]([CH3:23])([CH3:15])[O:17]2)=[CH:3][CH:4]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of (3S)-4-(4-bromophenyl)-3-methylmorpholine (630 mg), 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (630 mg) and triethylamine (1.03 mL) in 1,4-dioxane (10 mL) was added dichlorobis(triphenylphosphine)palladium(II) (86 mg), and the mixture was stirred overnight at 100° C. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water and 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 (470 mg).

Workup

extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed successively with water and 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-683d9265116544769f4bede4b709e3ee
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09371320B2

Reaction notes

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