Water → tert-butyl (Z)-4-[4-(methoxycarbonyl)-2-(prop-1-en-1-yl)phenyl]piperazine-1-carboxylate

HRID 1038531Notes

Reaction equation

I[C:2]1[CH:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[CH:4][C:3]=1[N:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]1.O.[CH:26](/B(O)O)=[CH:27]/[CH3:28].C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[CH3:11][O:10][C:8]([C:6]1[CH:5]=[CH:4][C:3]([N:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]2)=[C:2](/[CH:26]=[CH:27]\[CH3:28])[CH:7]=1)=[O:9]

Participants

Conditions

Temperature: 80 °C

Procedure

tert-Butyl 4-(2-iodo-4-(methoxycarbonyl)phenyl)piperazine-1-carboxylate (127 mg, 0.285 mmol) was dissolved in N,N-dimethylformamide:water=3:1 (2.8 mL). At room temperature, (Z)-propenylboronic acid (59 mg, 0.684 mmol), tetrakistriphenylphosphine palladium (16 mg, 0.0143 mmol) and sodium carbonate (121 mg, 1.14 mmol) were added sequentially, and the mixture was stirred at 80° C. for 1 hour, under microwave irradiation. The reaction solution was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The obtained residue was purified by silica-gel column chromatography (hexane/acetone). The title compound (96 mg (yield 94%)) was obtained as a yellow crystal.

Workup

extractionThe reaction solution was extracted with ethyl acetate
washThe organic layer was washed with brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated in vacuo
customThe obtained residue was purified by silica-gel column chromatography (hexane/acetone)

Sources & evidence

ORD record: ord-7e3c31117fe249579df46100a58cfe09
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08551985B2

Reaction notes

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