Water → HCID 46183174, compound

HRID 882714Notes

Reaction equation

[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].O.Br[C:20]1[CH:25]=[CH:24][C:23]([C:26]2([CH:29]3[N:32]([CH:33]4[CH:40]5[CH2:41][CH:36]6[CH2:37][CH:38]([CH2:42][CH:34]4[CH2:35]6)[CH2:39]5)[C:31](=[O:43])[C:30]3([CH3:45])[CH3:44])[CH2:28][CH2:27]2)=[CH:22][CH:21]=1>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:20]1([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:25]=[CH:24][C:23]([C:26]2([CH:29]3[N:32]([CH:33]4[CH:40]5[CH2:41][CH:36]6[CH2:37][CH:38]([CH2:42][CH:34]4[CH2:35]6)[CH2:39]5)[C:31](=[O:43])[C:30]3([CH3:45])[CH3:44])[CH2:28][CH2:27]2)=[CH:22][CH:21]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of 4-[1-(4-bromophenyl)cyclopropyl]-1-(adamantan-2-yl)-3,3-dimethylazetidin-2-one (12.2 mg, 0.0285 mmol) in 1,4-dioxane (3 mL) prepared in Example 75 was added with tetrakis(triphenylphosphine) palladium (1.6 mg, 1.4 μmol), phenyl boronic acid (7 mg, 0.057 mmol), and potassium phosphate (30 mg, 0.142 mmol) at room temperature, and the resultant was stirred at 100° C. for 20 hours. The reaction solution was poured into water, and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and concentrated in vacuo. The obtained residue was purified using thin-layer chromatography (hexane:ethyl acetate=3:1), and 4-[1-(biphenyl-4-yl)cyclopropyl]-1-(adamantan-2-yl)-3,3-dimethylazetidin-2-one (10.2 mg, 84%) was obtained as a white amorphous solid.

Workup

extractionextracted with ethyl acetate
dry with materialThe organic layer was dried over anhydrous sodium sulfate
concentrationconcentrated in vacuo
customThe obtained residue was purified

Sources & evidence

ORD record: ord-c53fa5005666456c9f8f811cab450f7c
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08236789B2

Reaction notes

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