4-Bromo-2,3-dimethylpyridine

2, 3-dimethylpyridin-4-ol, ( 2.0 g, 20 mmol) and phosphorus tribromide oxide (14.0 g, 49 mmol) were left stirring at 130A THF (75.0 mL) solution of EtOH (1.8 mL) was added into a mixture of 4-bromo-3-ethylpyridinehydrobromide (49 mg, 0.18 mmol), B2(OH)4 (49 mg, 0.55 mmol), XPhos-Pd-G2 (14 mg, 0.018 mmol), XPhos (17 mg, 0.037 mmol), and KOAc (54 mg, 0.55 mmol). The reaction was degassed via N2 and stirred at 80C overnight. After cooling to room temperature, solutions of N-(2-(3-bromophenyl)propan-2-yl)-2-(trifluoromethyl)benzenesulfonamide (Intermediate 1J) (100 mg, 0.24 mmol) in EtOH/THF (0.3 mL/0.3 mL) and K2C03 (1.8 M, 0.31 mL, 0.55 mmol) were added respectively into the reaction. The mixture was degassed via N2 again and stirred at 85C overnight. The reaction was cooled to room temperature, filtered through celite, washed with EtOAc (3X), and concentrated in vacuo to give a residue which was dissolved into EtOAc. This solution was washed with brine (IX), dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by MS-HPLC to afford the title compound (16 mg, 20%). LCMS (method A): m/z 449.3 (M+H)+. NMR (CDC13) delta 8.54 (s, 1H), 8.46 (d, 1H), 7.83 (d, 1H), 7.79 (d, 1H), 7.59 (t, 1H), 7.47 (t, 1H), 7.31 (m, 2H), 7.21 (t, 1H), 7.11 (dt, 1H), 7.03 (d, 1H), 5.28 (s, 1H), 2.63 (q, 2H), 1.69 (s, 6H), 1.13 (t, 3H).General procedure: Intermediate 10 (0.1 g, 0.26 mmol), bispinacolatodiboron (0.13 g, 0.52 mmol), [l, l'Bis(diphenylphosphino) ferrocene] palladium(II) dichloride (0.042 g, 0.052 mmol), and potassium acetate (0.076 g, 0.77 mmol) were mixed in dioxane (2 mL) in a pressure vessel and heated to 80C for 18 hours. The reaction was cooled to room temperature and 4-bromo-2-methylpyridine hydrochloride (0.081 g, 0.39 mol) and [Iota, Gamma- Bis(diphenylphosphino)ferrocene]-palladium(II) dichloride (0.042 g, 0.052 mmol) were added, followed by addition of 1M tribasic potassium phosphate solution (1 mL). The reaction was heated to 80C ovemight. The resultant mixture was filtered over celite and diluted with DCM, and washed with H20 (lx) and brine (lx). The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo.. The residue was purified by flash chromatography (10 - 70% EtOAc/hexanes) to afford Compound 7 (0.65 g, 65%). LCMS (method A): m/z 401.4/403.4 (M+H)+. 1HNMR (CD3OD): delta 8.42 (s, 1H), 8.38 (d, IH), 7.75 (dd, IH), 7.45 (dd, IH), 7.26 (t, IH), 7.18-7.10 (m, 4H), 7.02 (t, IH), 4.48 (q, IH), 2.51 (s, 3H), 2.21 (s, 3H), 1.46 (d, 3H)2, 3-dimethylpyridin-4-ol, ( 2.0 g, 20 mmol) and phosphorus tribromide oxide (14.0 g, 49 mmol) were left stirring at 1300C for 4 hours under nitrogen. The reaction mixture was poured onto ice and made basic by adding aqueous NaOH. The mixture was then extracted with diethyl ether and water.The brown needle solid was obtained after ether was gently removed (2.03g, purity 90%, yield 60%). 1HNMR (CDCI3): delta ppm 8.10 (d, 1 H), 7.34 (d, 1 H), 2.58 (s, 3H), 2.39 (s, 3H). LC/MS: rt (5-100-7 method) =3.555 min.; 185.7 (M+1 , 100 %) 187.7 (M+3, 97%).

Molecular Weight:186.05
XLogP3:2.3
Hydrogen Bond Acceptor Count:1
Exact Mass:184.98401
Monoisotopic Mass:184.98401
Topological Polar Surface Area:12.9
Heavy Atom Count:9
Complexity:94.9
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes