[CH2:1]([N:5]([C:12]1[C:13](I)=[N:14][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:16][CH:17]=1)C(=O)C(F)(F)F)[CH:2]=[CH:3][CH3:4].O>CN(C=O)C.[N+](CCCC)(CCCC)(CCCC)CCCC.[Cl-].CC([O-])=O.CC([O-])=O.[Pd+2]>[CH2:3]([C:2]1[C:13]2=[N:14][C:15]([C:18]([F:19])([F:20])[F:21])=[CH:16][CH:17]=[C:12]2[NH:5][CH:1]=1)[CH3:4]
A solution of N-but-2-enyl-2,2,2-trifluoro-N-(2-iodo-6-trifluoromethyl-pyridin-3-yl)-acetamide (5.2 g, 11.9 mmol) in DMF (24 mL) is treated with n-Bu4NCl (3.6 g, 13.1 mmol), Pd(OAc)2 (107 mg, 0.48 mmol), and stirred at 100° C. for 1 h. H2O (10 mL) is added, and the mixture is cooled to rt and filtered through a pad of silica gel. The filtrate is extracted with EtOAc/heptane (3×50 mL) (1:1). The combined organic layer is dried (Na2SO4), filtered and concentrated in vacuo. The residue is purified by silica gel chromatography eluting with 5%-50% EtOAc in heptane to afford 3-ethyl-5-trifluoromethyl-1H-pyrrolo[3,2-b]pyridine (2.2 g, 86%). MS: 215 (M+H); 1H NMR (300 MHz, CDCl3): δ 8.24 (s, NH, 1H), 7.73 (d, 1H), 7.50 (d, 1H), 7.34 (d, 1H), 2.93 (q, 2H), 1.36 (t, 3H).
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