Sodium Carbonate → HCID 68539930, compound

HRID 1931405Notes

Reaction equation

HRID 1931405 reaction equation
[C:1]([O:5][C:6](=[O:16])[CH2:7][O:8][C:9]1[N:14]=[CH:13][C:12](Br)=[CH:11][N:10]=1)([CH3:4])([CH3:3])[CH3:2].[F:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1B(O)O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]([O:5][C:6](=[O:16])[CH2:7][O:8][C:9]1[N:14]=[CH:13][C:12]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[F:17])=[CH:11][N:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 27343542-Fluorophenylboronic acidHCID 68539644HCID 68539644, compound

Product 1

HCID 68539930HCID 68539930, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

500 mg (1.73 mmol) of (5-bromo-pyrimidin-2-yloxy)-acetic acid tert -butyl ester from step (a), 190.4 mg (2.07 mmol) of 2-fluorophenylboronic acid, 19.4 mg (0.086 mmol) of palladium acetate, 45.4 mg (0.17 mmol) of triphenylphosphine and 1.07 ml of an aqueous 1 M sodium carbonate solution in 40 ml of toluene were heated under reflux for 8 h. After cooling, the mixture was poured onto water and extracted with ethyl acetate. The combined organic phases were dried and evaporated. Yield: 335 mg.

Workup

  1. temperatureunder reflux for 8 h
  2. temperatureAfter cooling
  3. additionthe mixture was poured onto water
  4. extractionextracted with ethyl acetate
  5. customThe combined organic phases were dried
  6. customevaporated

Sources & evidence

ORD record
ord-9f832d7d0641458a88392e6f5e7eafe1
Source dataset
uspto-grants-2012_05
Patent number
US08188291B2

Reaction notes

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