Toluene → HCID 66685360, compound

HRID 922263Notes

Reaction equation

HRID 922263 reaction equation
C1(C)C=CC=CC=1.[CH3:8][C:9]1[C:13](B(O)O)=[C:12]([CH3:17])[O:11][N:10]=1.Br[C:19]1[CH:24]=[C:23]([O:25][CH3:26])[CH:22]=[CH:21][C:20]=1[CH2:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30].C(=O)(O)[O-].[Na+]>CCO.[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>[CH3:8][C:9]1[C:13]([C:21]2[CH:22]=[C:23]([O:25][CH3:26])[CH:24]=[CH:19][C:20]=2[CH2:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])=[C:12]([CH3:17])[O:11][N:10]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 516892Sodium BicarbonateHCID 27343463,5-Dimethylisoxazole-4-boronic acidHCID 66684913HCID 66684913, compound

Product 1

HCID 66685360HCID 66685360, compoundYield 94.2%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
95 °C

Procedure

To a 25 mL RB flask fitted with a magnetic stirrer was charged with Toluene (1 mL). To the stirred solvent were added (3,5-dimethyl-1,2-oxazol-4-yl)boronic acid (0.059 g, 0.42 mmol), ethyl 3-(2-bromo-4-methoxyphenyl)propanoate (0.08 g, 0.28 mmol), sodium bicarbonate (0.5 mL, 2M solution) in ethanol (1 mL) under argon atmosphere. After addition, the reaction mixture was purged with argon for 15 minutes. To the reaction mixture was added tetrakis (triphenylphosphine) palladium (0) (0.016 g, 0.01 mmol) and purged with argon for 10 minutes. After addition, the reaction mixture was heated at 95° C. for 5 h under argon atmosphere. After completion of the reaction, the reaction mixture was quenched with water (10 mL) and extracted with ethyl acetate (10 mL). The organic layer was washed with water (5 mL) and brine solution (5 mL). The organic layer was dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure. The crude product (0.08 g, yield: 94.10%) was taken for next step with out purification.

Workup

  1. customTo a 25 mL RB flask fitted with a magnetic stirrer
  2. additionAfter addition
  3. customthe reaction mixture was purged with argon for 15 minutes
  4. custompurged with argon for 10 minutes
  5. additionAfter addition
  6. customAfter completion of the reaction
  7. customthe reaction mixture was quenched with water (10 mL)
  8. extractionextracted with ethyl acetate (10 mL)
  9. washThe organic layer was washed with water (5 mL) and brine solution (5 mL)
  10. dry with materialThe organic layer was dried over anhydrous Na2SO4
  11. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-daf7c6bf495147bf88bc04962d2b1943
Source dataset
uspto-grants-2016_03
Patent number
US09278915B2

Reaction notes

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