2-CHLORO-4-PHENYLPYRIDINE

General procedure: 2-bromo-6-chloropyridine (21.2 g, 0.11 mol)Phenylboronic acid (12.2 g, 0.10 mol)Palladium tetrakis triphenylphosphine 0.5g, Add to 1000ML reaction flask, add toluene 400ML, Aqueous sodium carbonate solution (2N, 150 mL) was treated with nitrogen and the oil bath was reacted at 80 ° C for 24 hours.Post-treatment: cooling, static 30 minutes to remove the liquid, keep the organic layer, spin dry toluene, solid plus dichloromethane dissolved, column separation, PE: DCM = 1: 1 column, was A-1 (9.6g, Y = 51percent)To a mixture of (S)-tert-butyl 2-amino-4-(((S)-2-fluoro-3-methoxypropyl) (4-(5, 6, 7, 8-tetrahydro-1, 8-naphthyridin-2-yl) butyl)amino) butanoate (150 mg, 331 mumol) and To a 250 mL round bottom flask were added intermediate 1 (4.4 g, 23 mmol), intermediate 7 (6.6 g, 19 mmol), 17 Pd(OAc)2 (213 mg, 0.95 mmol), Sphos (780 mg, 1.9 mmol), 18 potassium carbonate (3.9 g, 28.5 mmol), 19 toluene (60 mL) and 20 water (20 mL), and then the resulting mixture was bubbled with 14 N2 for 5 min. Then the reaction was heated to reflux overnight under the protection of N2. The reaction mixture was cooled to room temperature after the finish monitored by TLC, and water and EA were added. The reaction was extracted, and the organic phase was combined, dried over MgSO4, evaporated to dryness, and purified via silica gel column chromatography, eluting with DCM:PE=2:1 (v:v), to afford intermediate 8 (3.2 g, 45% yield) as a white powderTo a 500 mL three-necked flask were added intermediate 1 (8 g, 42.3 mmol), 9, 9-dimethylfluorene-2-boronic acid pinacol ester (14.7 g, 46.5 mmol), Pd(PPh3)4 (2.4 g, 2.1 mmol), potassium carbonate (17.5 g, 126 mmol), toluene (200 mL) and water (70 mL), and then the resulting reaction mixture was heated to reflux for 12 h under N2 protection. The reaction solution was cooled to room temperature after the finish of the reaction monitored by TLC, separated, the organic phase was collected, the water phase was extracted with EA for several times, and the organic phase was combined, dried with MgSO4 and evaporated to dryness, purified via silica gel column chromatography, eluting with EA:PE=1:50 (v:v), to afford intermediate 2 (4 g, 27% yield) as a white solid.In a 50 mL round bottom flask, 1.89 g of General procedure: The aryl halide was dissolved in 5mL of methanol per mmol of (hetero)arylhalide, magnesium (5 equiv.) added and the mixture was stirred at room temperature. After completion of the reaction (between 6-12h), the reaction mixture was poured into water, acidified with dilute HCl, and extracted with ethyl acetate. The organic phase was dried over MgSO4 and concentrated under reduced pressure. The product was purified if necessary by column chromatography on silica gel.

Molecular Weight:189.64
XLogP3:3.4
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:189.0345270
Monoisotopic Mass:189.0345270
Topological Polar Surface Area:12.9
Heavy Atom Count:13
Complexity:154
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes