Tetrahydrofuran → HCID 86725257, compound

HRID 2208587Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][N:6]([C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])[CH2:5]2.[F-].[Cs+].[CH2:23]1[CH2:27]OC[CH2:24]1.C(B1OC(C)(C)C(C)(C)O1)C=C>C(OCC)(=O)C>[CH2:27]([C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][N:6]([C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])[CH2:5]2)[CH:23]=[CH2:24]

Participants

Conditions

Temperature: 72 °C

Procedure

To a mixture of benzyl 5-bromoisoindoline-2-carboxylate (332 mg, 1 mmol), tetrakistriphenylphosphine palladium (0) (80 mg, 0.07 mmol), and cesium fluoride (604 mg, 4 mmol) was added THF (7 mL). The system was degassed and flushed with argon. To this mixture was added allyl boronic acid pinacol ester (285 μL, 1.5 mmol). The resulting mixture was heated to 72° C. and stirred at this temperature for 4 hr then cooled to room temperature. The mixture was diluted with ethyl acetate, washed with brine, dried over magnesium sulfate and concentrated under vacuum. The residue was purified by silica chromatography (25 g silica eluted with 3-40% ethyl acetate in hexane) to give the title compound as a white solid.

Workup

customThe system was degassed
customflushed with argon
temperaturethen cooled to room temperature
washwashed with brine
dry with materialdried over magnesium sulfate
concentrationconcentrated under vacuum
customThe residue was purified by silica chromatography (25 g silica eluted with 3-40% ethyl acetate in hexane)

Sources & evidence

ORD record: ord-ea20315fed8a4cc08a049af701580fd9
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09376454B2

Reaction notes

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