Potassium Phosphate, Tribasic → HCID 58042373, compound
Reaction equation
Br[C:2]1[C:7]([O:8][C:9]([F:12])([F:11])[F:10])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH:13]1(B(O)O)[CH2:15][CH2:14]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>C1(C)C=CC=CC=1.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:13]1([C:2]2[C:7]([O:8][C:9]([F:12])([F:11])[F:10])=[CH:6][CH:5]=[CH:4][N:3]=2)[CH2:15][CH2:14]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 95 °C
Procedure
A solution of 2-bromo-3-(trifluoromethoxy)pyridine (Preparation 247, 776 mg, 3.21 mmol), cyclopropyl boronic acid (331 mg, 3.85 mmol) and potassium phosphate tribasic (1.70 g, 8.02 mmol) in toluene (10 mL) and water (3 mL) was degassed with nitrogen for 15 minutes at 80° C. Palladium acetate (36 mg, 0.16 mmol) and tricyclohexyl phosphine (90 mg, 0.32 mmol) were added and the reaction mixture was vigorously stirred for 18 hours at 95° C. under nitrogen. The solution was concentrated in vacuo, diluted with water (25 mL) and extracted with ethyl acetate (3×30 mL). The organic layers were combined, dried over magnesium sulfate, filtered and concentrated in vacuo. The crude material was purified by silica gel column chromatography eluting with 10% diethyl ether in heptane to afford the title compound as a colourless oil (292 mg, 45%).
Workup
- concentrationThe solution was concentrated in vacuo
- additiondiluted with water (25 mL)
- extractionextracted with ethyl acetate (3×30 mL)
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe crude material was purified by silica gel column chromatography
- washeluting with 10% diethyl ether in heptane
Sources & evidence
- ORD record
- ord-1380c4fed39f4488bd6cdb55d7e17698
- Source dataset
- uspto-grants-2013_11
- Patent number
- US08592629B2
Reaction notes
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