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]1A 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).
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