Potassium Phosphate, Tribasic → HCID 69311702, compound

HRID 1880575Notes

Reaction equation

HRID 1880575 reaction equation
Cl[C:2]1[CH:3]=[C:4]([C:8](=[CH2:12])[CH2:9][CH2:10][OH:11])[CH:5]=[CH:6][CH:7]=1.[F:13][C:14]([F:26])([F:25])[O:15][C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2)CCCCC1>CC([O-])=O.CC([O-])=O.[Pd+2].C1(C)C=CC=CC=1>[F:13][C:14]([F:25])([F:26])[O:15][C:16]1[CH:21]=[CH:20][C:19]([C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([C:8](=[CH2:12])[CH2:9][CH2:10][OH:11])[CH:3]=2)=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 27342162-(Dicyclohexylphosphino)biphenylHCID 27343864-(Trifluoromethoxy)phenylboronic acidHCID 67487863HCID 67487863, compound

Product 1

HCID 69311702HCID 69311702, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A toluene solution (5 mL) containing the intermediate from Step A (441 mg, 2.4 mmol), 4-(trifluoromethoxy)phenyl boronic acid (746 mg, 3.62 mmol), K3PO4 (865 mg, 4.08 mmol), 2-(dicyclohexylphosphino)biphenyl (68 mg, 0.19 mmol) and Pd(OAc)2 (22 mg, 0.098 mmol) was heated at 100° C. under an argon atmosphere. After 1 hour the solution was partitioned between water and ethyl acetate. The organic phase washed with 1N NaOH, brine, dried over MgSO4 and concentrated. The residue was purified by silica gel chromatography using a hexanes/ethyl acetate gradient to give the title compound. LCMS1 3.71 min. (M+H)=309.

Workup

  1. customAfter 1 hour the solution was partitioned between water and ethyl acetate
  2. washThe organic phase washed with 1N NaOH, brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-a6264544df2c499c95ee4efe627039da
Source dataset
uspto-grants-2012_11
Patent number
US08318760B2

Reaction notes

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