Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH2:13][CH2:12][CH2:11][CH2:10][C:9]=2[C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[CH:5]=[CH:4][N:3]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2)CCCCC1.[Li+].C[Si]([N-:51][Si](C)(C)C)(C)C.[Cl-].[NH4+]>C1COCC1>[F:20][C:17]1[CH:18]=[CH:19][C:14]([C:9]2[CH2:10][CH2:11][CH2:12][CH2:13][C:8]=2[C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH2:51])[CH:7]=2)=[CH:15][CH:16]=1
A sealed 8 mL vial is charged with 2-Chloro-4-[2-(4-fluoro-phenyl)-cyclohex-1-enyl]-pyridine (25 mg, 0.087 mmol), Tris(dibenzyldieneacetone)Dipalladium (15.9 mg, 0.017 mmol) and 2-(dicyclohexylphosphino)biphenyl (15.8 mg, 0.045 mmol) in dry THF (3 mL). Argon is bubbled through the mixture for 5 min. Additional THF (1 mL) and LiHMDS (1.0 M in toluene, 0.26 mL, 0.26 mmol) are added. And the resulting mixture is allowed to stir at 65° C. for 1 hour. To the mixture is added saturated ammonium chloride solution and extracted with EtOAc (10 mL×3). The organic extract are washed with water (10 mL×1) and brine (10 mL×1), and dried over anhydrous sodium sulfate. After concentration, the crude is purified by silica flash column chromatography using MeOH in DCM (gradient from 0% to 10%) to give 11 mg of the desired product.
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