Potassium Phosphate, Tribasic → HCID 59612868, compound

HRID 532858Notes

Reaction equation

HRID 532858 reaction equation
FC(F)(F)S(O[C:7]1[CH:16]=[C:15]2[C:10]([CH:11]=[CH:12][CH:13]=[N:14]2)=[CH:9][CH:8]=1)(=O)=O.[CH:19]1(B(O)O)[CH2:21][CH2:20]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>C1(C)C=CC=CC=1.O.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH:19]1([C:7]2[CH:16]=[C:15]3[C:10]([CH:11]=[CH:12][CH:13]=[N:14]3)=[CH:9][CH:8]=2)[CH2:21][CH2:20]1

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 2760897Cyclopropylboronic acidHCID 59296115Quinolin-7-yl trifluoromethanesulfonate

Product 1

HCID 59612868HCID 59612868, compoundYield 61%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
105 °C

Procedure

A mixture of quinolin-7-yl trifluoromethanesulfonate (9.28 g, 33.5 mmol), cyclopropylboronic acid (3.74 g, 43.55 mmol), K3PO4 (24.9 g, 117.2 mmol), tricyclohexylphosphine (0.94 g, 3.35 mmol), and Pd(OAc)2 (0.376 g, 1.67 mmol) in toluene (200 mL) and water (10 mL) was heated overnight at 105° C. under an atmosphere of N2. The mixture was filtered through a plug of celite, and the filtrate was collected and extracted with EtOAc/brine. The organic layer was separated, dried over anhydrous Na2SO4, concentrated, and purified by chromatography (SiO2) with a gradient elution of 1-15% EtOAc/CH2Cl2 to yield 7-cyclopropylquinoline (3.45 g, 61% yield).

Workup

  1. filtrationThe mixture was filtered through a plug of celite
  2. customthe filtrate was collected
  3. extractionextracted with EtOAc/brine
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated
  7. custompurified by chromatography (SiO2) with a gradient elution of 1-15% EtOAc/CH2Cl2

Sources & evidence

ORD record
ord-f60a17ec2fcb4ec0b552215e2431fb80
Source dataset
uspto-grants-2014_10
Patent number
US08853202B2

Reaction notes

Loading…