[2,3']bipyridinyl-4-ylamine

(ii) Suzuki reaction of aryl halides (in water) Preparation of the catalyst-stock-solution: The catalyst stock solution was prepared as described for the aqueous Sonogshira reaction using 9-Et-2-SOGeneral procedure: 2-Bromopyridin-4-amine (150 mg, 0.86 mmol), 11 phenylboronic acid (211.4 mg, 1.73 mmol) and [1, 1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) (42.46 mg, 0.054 mmol) were suspended in a mixture of 12 Cs2CO3 2M in 13 water (1.3 mL, 2.60 mmol) and 6.5 mL of 14 1, 4-Dioxane. The reaction mixture was degassed and the vial was sealed and heated at 110C overnight. The reaction was quenched with 15 NaOH 1 M and extracted two times with ethyl acetate. The organic layer was washed (NaHCO3 saturated and Brine), dried with sodium sulphate and concentrated under vacuum. The crude was purified by CombiFlash column chromatography (Cyclohexane: Ethyl Acetate) to obtain the 16 amine derivative (91.2 mg, 61.8%). 1H-NMR (400 MHz, DMSO-d6): delta = 8.08 (d, 1 H), 7.90 (d, 2H), 7.44 (t, 2H), 7.37 (t, 1 H), 6.99 (d, 1 H), 6.45 (dd, 1 H), 6.07 (s, 2H). HPLC-MS: Rt 3.014; m/z 170.9 (MH+).(ii) Suzuki reaction of aryl halides (in water) Preparation of the catalyst-stock-solution: The catalyst stock solution was prepared as described for the aqueous Sonogshira reaction using 9-Et-2-SO3HFlu-PCy2-HBF4 (13a). Cross-coupling reaction: Aryl halide (1 mmol), boronic acid (1.2 mmol) and K2CO3 (3.2 mmol) were first added to water (4 ml), then the catalyst stock solution and two drops of Labrasol (caprylocaproyl macrogol-8 glyceride blend, saturated polyglycolized glycerides consisting of mono-, di-and triglycerides of mono- and di-fatty acids of polyethylene glycol (PEG)) were added. The reaction mixture was stirred at the respective temperatures (see Table 8) for 0.5-20 h (see Table 8). After cooling to room temperature the reaction mixture was diluted with ether (15 ml), washed with water (10 ml), the organic phase was dried over MgSO4, filtered and concentrated in vacuo. The product was isolated by column chromatography (silica, cyclohexane / ethylacetate (100:2). Alternatively the yield was determined via gas chromatography with hexadecane or diethylene glycol di-n-butylether as an internal standard.

Molecular Weight:171.20
XLogP3:0.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:171.079647300
Monoisotopic Mass:171.079647300
Topological Polar Surface Area:51.8
Heavy Atom Count:13
Complexity:160
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes