Sodium Carbonate → HCID 67170582, compound

HRID 1475789Notes

Reaction equation

HRID 1475789 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:8]2[CH2:11][O:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([O:22][CH3:23])=[O:21])=[CH:16][C:15]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CC(=O)OCC.O.CN(C=O)C>[CH3:23][O:22][C:20]([C:17]1[CH:16]=[C:15]([C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([CH:8]3[CH2:11][O:10][CH2:9]3)[CH:3]=2)[C:14]([O:13][CH3:12])=[CH:19][CH:18]=1)=[O:21]

Participants

9

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 9837205(2-Methoxy-5-(methoxycarbonyl)phenyl)boronic acidHCID 534843193-(3-Bromophenyl)oxetane

Product 1

HCID 67170582HCID 67170582, compoundYield 71.4%

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

1.3 g of 3-(3-bromo-phenyl)-oxetane, 1.3 g of 2-methoxy-5-methoxycarbonylphenylboronic acid, 1.3 g of Na2CO3, 69 mg of palladium(II)acetate, and 160 mg of triphenylphosphine were combined and 15 ml of DMF and 1 ml of water added. The mixture was stirred at 100° C. for 1 h and then allowed to cool to room temperature. 100 ml of EA were then added and washed three times using 30 ml of water each. The organic layer was then dried using MgSO4 and evaporated. Chromatography on silica gel using EA/HEP 1:3 yielded 1.3 g of the title compound, colorless oil.

Workup

  1. temperatureto cool to room temperature
  2. washwashed three times
  3. customThe organic layer was then dried
  4. customevaporated

Sources & evidence

ORD record
ord-1fbd5366a2454335ac747888eb95d6e1
Source dataset
uspto-grants-2015_04
Patent number
US09018383B2

Reaction notes

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