Potassium Phosphate, Tribasic → HCID 86657754, compound

HRID 383776Notes

Reaction equation

HRID 383776 reaction equation
I[C:2]1[CH:7]=[C:6]([C:8]([N:10]2[CH2:14][CH2:13][CH:12]([C:15]3[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=3)[CH2:11]2)=[O:9])[CH:5]=[CH:4][C:3]=1[C:21]1[CH:26]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:24]=[C:23]([C:31]([F:34])([F:33])[F:32])[CH:22]=1.[CH:35]1(B(O)O)[CH2:37][CH2:36]1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.CCOC(C)=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH:35]1([C:2]2[CH:7]=[C:6]([C:8]([N:10]3[CH2:14][CH2:13][CH:12]([C:15]4[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=4)[CH2:11]3)=[O:9])[CH:5]=[CH:4][C:3]=2[C:21]2[CH:26]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:24]=[C:23]([C:31]([F:34])([F:33])[F:32])[CH:22]=2)[CH2:37][CH2:36]1

Participants

9

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 2760897Cyclopropylboronic acidHCID 86657755HCID 86657755, compound

Product 1

HCID 86657754HCID 86657754, compound

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

Palladium acetate (8.00 mg, 0.036 mmol) was added to a solution of 4b (210 mg, 0.356 mmol), cyclopropylboronic acid (36.7 mg, 0.427 mmol), tricyclohexylphosphine (20.0 mg, 0.071 mmol) and potassium phosphate tribasic (227 mg, 1.07 mmol) in toluene:water (3.15 mL of an 20:1 mixture, respectively) at rt. The resulting solution was heated to 100° C. After approximately 24 h, the reaction was cooled to rt, diluted with EtOAc and filtered through a short column of Celite®, eluting with EtOAc. The resulting crude residue was purified by column chromatography on silica gel (gradient elution; 0%-1% methanol/EtOAc as eluent) to afford the title compound 4c. m/z (ES) 505 (MH)+.

Workup

  1. customat rt
  2. temperaturethe reaction was cooled to rt
  3. filtrationfiltered through a short column of Celite®
  4. washeluting with EtOAc
  5. customThe resulting crude residue was purified by column chromatography on silica gel (gradient elution; 0%-1% methanol/EtOAc as eluent)

Sources & evidence

ORD record
ord-b3584d4779dc42a8a321e9cd8bc0fb2f
Source dataset
uspto-grants-2013_02
Patent number
US08367679B2

Reaction notes

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