FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[C:8]=1[C:16]#[N:17])(=O)=O.[B-](F)(F)(F)[C:21]([CH3:23])=[CH2:22].[K+].C(=O)([O-])[O-].[Cs+].[Cs+]>C1COCC1.O.CCOC(C)=O.[Pd+2].ClC1C=C[C-](P(C2C=CC=CC=2)C2C=CC=CC=2)C=1Cl.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[N+:13]([C:9]1[CH:10]=[CH:11][CH:12]=[C:7]([C:21]([CH3:23])=[CH2:22])[C:8]=1[C:16]#[N:17])([O-:15])=[O:14]A suspension of 2-cyano-3-nitrophenyl trifluoromethanesulfonate (Example 129d) (0.93 g, 3.15 mmol), potassium trifluoro(prop-1-en-2-yl)borate (0.70 g, 4.73 mmol), dichloro 1,1′-bis(diphenylphosphino)ferrocene palladium(II) (0.26 g, 0.32 mmol), cesium carbonate (3.08 g, 9.45 mmol) and water (5.6 mL) in THF (56 mL) was heated at reflux for 25 min, under a nitrogen atmosphere. The reaction mixture was cooled to room temperature and diluted with water (100 mL) and EtOAc (100 mL). The organic phase was separated and the aqueous phase was extracted with EtOAc (3×100 mL). The combined extract was washed with diluted HCl (1.5M), brine and dried with anhydrous MgSO4. The filtrate was evaporated and the residue was purified by chromatography on silica gel using gradient hexanes to hexanes/EtOAc (7:3), to give 0.30 g (49%) of the title compound as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 8.24-8.29 (m, 1H), 7.86-7.95 (m, 2H), 5.47-5.52 (m, 1H), 5.20-5.23 (m, 1H), 2.12-2.15 (m, 3H).
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