Potassium Phosphate, Tribasic → HCID 57706456, compound

HRID 2098895Notes

Reaction equation

HRID 2098895 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[O:10][C:11]([F:14])([F:13])[F:12].[F:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][C:17]=1B(O)O.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1>CCOC(C)=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1COCC1.CN(C=O)C>[F:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][C:17]=1[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[O:10][C:11]([F:14])([F:13])[F:12]

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 41572112-Fluoro-5-methoxyphenylboronic acidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 177507904-Chloro-3-(trifluoromethoxy)benzaldehyde

Product 1

HCID 57706456HCID 57706456, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 8857Ethyl AcetateSolventHCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

A screw-cap vial was charged with 4-chloro-3-(trifluoromethoxy)benzaldehyde (available from Alfa Aesar, Avocado, Lancaster) (0.184 g, 0.82 mmol), 2-fluoro-5-methoxyphenylboronic acid (available from Aldrich) (0.278 g, 1.64 mmol), potassium phosphate (0.522 g, 2.46 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (0.101 g, 0.25 mmol), palladium(II) acetate (0.018 g, 0.082 mmol), and 5:1 THF/DMF (3.6 mL). The mixture was stirred overnight at 40° C., cooled to room temperature, diluted with EtOAc, washed with water and brine, dried (MgSO4), and concentrated. The residue was chromatographed on silica gel (0-10% EtOAc/hexane) to afford K.1 (165 mg, 64%) as a colorless oil.

Workup

  1. temperaturecooled to room temperature
  2. washwashed with water and brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue was chromatographed on silica gel (0-10% EtOAc/hexane)
  6. customto afford K.1 (165 mg, 64%) as a colorless oil

Sources & evidence

ORD record
ord-7e29f257ff7c436fb1e870ac25e6f86d
Source dataset
uspto-grants-2013_05
Patent number
US08450522B2

Reaction notes

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