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(5-bromo-6-chloropyrazin-2-yl)[(4-methoxyphenyl)methyl] amine[ No CAS ]
[ 290832-43-8 ]
[ 1100873-14-0 ]
Yield
Reaction Conditions
Operation in experiment
With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; at 80℃; for 16h;
B. In a pressure tube, a mixture of the product from step A (1 equivalent), 2- methoxy-5-trifluoromethoxyphenylboronic acid (1.6 equivalents) and Pd [(PPH3)] 4 (0.04 equivalents) in toluene (4 ml/mmol of product from step A), ethanol (. 2 ml/mmol of product from step A) and aqueous [K2CO3] (2M, 2 [ML/MMOL] of product from step A) is heated to [80C] for 16 hours. The mixture is diluted with ethyl acetate, and the organic fraction washed with NaOH (2M, 20 mL/mmol of product from step A) and brine (3 x 20 ml/mmol of product from step A), then dried [(MGS04),] filtered and the solvent removed under reduced pressure. Chromatography of the residue provides [(3- (2-METHOXY-5-TRIFLUOROMETHOXYPHENYL)-6-] chloropyrazin-2-yl) [ (4-methoxyphenyl) methyl] amine.
To a cooled (-300C) solution of <strong>[710-18-9]1-methoxy-4-(trifluoromethoxy)benzene</strong> (960mg, 5mmol) in THF (1OmL) was added n-BuLi (2.5M in hexane) (2.2OmL, 5.50mmol) over 10 min. The reaction mixture was stirred for 30 min, cooled to -78 0C and triisopropylborane (1.3Og, 7.0mmol) was added over 5 min. The reaction mixture was stirred for 1 h at -78 C and 1 M hydrochloric acid solution (6mL) was added. After warming to rt, the mixture was stirred vigorously for 30 min. The phases were separated and the aqueous phase was extracted with EtOAc. The organic phase was washed with water, brine, dried over magnesium sulfate and the solvent was removed in vacuo to give the crude residue. Trituration with hexane afforded the desired product as a white solid, 450mg (38%). LRMS (APCI) 235 [MH"]
To a solution of the compound of preparation 21 (450mg, 1.90mmol) in water (3mL) was added sodium hydroxide (114mg, 2.85mmol), sodium hydrogen carbonate (1.6Og, 19.0mmol), acetone (4mL) and EDTA (58mg, 0.2mmol) at rt. The mixture was cooled to 0 0C and Oxone (1.3Og, 2.10mmol) was added portionwise over 5 min. The mixture was warmed to rt and stirred for 2h. 2M hydrochloric acid solution (15mL) was added and the phases were separated. The aqueous phase was extracted with EtOAc, the organic extract was dried over magnesium sulfate and the solvent was removed in vacuo to afford the desired product as a yellow oil, 277mg (70%). EPO <DP n="29"/>LRMS (APCI) 207 [MH"]
(5-bromo-6-chloropyrazin-2-yl)[(4-methoxyphenyl)methyl] amine[ No CAS ]
[ 584-08-7 ]
[ 290832-43-8 ]
[ 1100873-13-9 ]
Yield
Reaction Conditions
Operation in experiment
Pd(PPh3)4; In ethanol; toluene;
B. In a pressure tube, a mixture of the product from step A (1 equivalent), 2-methoxy-5-trifluoromethoxyphenylboronic acid (1.6 equivalents) and Pd(PPh3)4 (0.04 equivalents) in toluene (4 ml/mmol of product from step A), ethanol (0.2 ml/ mmol of product from step A) and aqueous K2CO3 (2M, 2 ml/mmol of product from step A) is heated to 80 C. for 16 h. The mixture was diluted with ethyl acetate, and the organic fraction washed with NaOH (2M, 20 mL/mmol of product from step A) and brine (3*20 ml/mmol of product from step A), then dried (MgSO4), filtered and the solvent removed under reduced pressure. Chromatography of the residue provided (3-(2-methoxy-5-trifluoromethoxyphenyl)-6-chloropyrazin-2-yl)[(4-methoxyphenyl)methyl]amine.
A suspension of 2-methoxy-5-(trifluoromethoxy)phenylboronic acid (23.0 g, 97.5 mmol) in dichloromethane (140 ml_) was cooled to 0 C and boron tribromide (9.4 ml_,10 mmol) was added drop-wise over 30 min. After stirring for 3 hours, additional boron tribromide (2 ml_) was added. The reaction mixture was poured into ice water and stirred for 20 min. The dichloromethane was removed in vacuo and the white solid collected by filtration and washed with water before drying in vacuo to afford the title compound(20.8 g). HNMR (d4-Methanol): δ 6.78 (d, 1 H), 7.1 1 (d, 1 H), 7.40 (br s, 1 H).LCMS Rt = 1 .67 min MS m/z 221 [M-H]-
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