Water → HCID 66598182, compound

HRID 1038521Notes

Reaction equation

HRID 1038521 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][N:14]([C:17]2[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][C:18]=2Br)[CH2:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[CH:29](/B(O)O)=[CH:30]/[CH3:31].C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[CH2:1]([O:8][CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][N:14]([C:17]2[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][C:18]=2/[CH:29]=[CH:30]\[CH3:31])[CH2:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 5355539(Z)-Prop-1-en-1-ylboronic acidHCID 66598423HCID 66598423, compound

Product 1

HCID 66598182HCID 66598182, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Methyl 4-{4-[2-(benzyloxy)ethyl]piperazin-1-yl}-3-bromobenzoate (78 mg, 0.180 mmol) was dissolved in N,N-dimethylformamide: water=3:1 (1.8 mL). At room temperature, (Z)-propenylboronic acid (containing about 10% E-isomer; Hereinafter the same is used for all) (37 mg, 0.433 mmol), tetrakistriphenylphosphine palladium (10 mg, 0.00902 mmol) and sodium carbonate (76 mg, 0.722 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 (61 mg (yield 86%)) was obtained as a yellow oil.

Workup

  1. additionwere added sequentially
  2. extractionThe reaction solution was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe obtained residue was purified by silica-gel column chromatography (hexane/acetone)

Sources & evidence

ORD record
ord-304644001092478480dfee33cd9c392b
Source dataset
uspto-grants-2013_10
Patent number
US08551985B2

Reaction notes

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