반응 #168219

반응 방정식

N,N-Dimethylacetamide

2,3-dichloro-5-(4-phenoxyphenyl)isonicotinonitrile

4-methoxyphenylboronic acid

potassium phosphate

→

3-chloro-2-(4-methoxyphenyl)-5-(4-phenoxyphenyl)isonicotinonitrile

수율 55.2%

용매

ethyl acetate

반응 조건

후처리

1. 1
   기타The reaction tube was sealed
2. 2
   세척washed with 1:1 mixture of brine and water (15 mL), brine (15 mL)
3. 3
   건조dried (MgSO4)
4. 4
   농축concentrated
5. 5
   세척eluting with 5-30% ethyl acetate in hexanes

실험 절차

A mixture of 2,3-dichloro-5-(4-phenoxyphenyl)isonicotinonitrile (109 mg, 0.319 mmol), 4-methoxyphenylboronic acid (58.3 mg, 0.383 mmol), potassium phosphate (136 mg, 0.639 mmol) and palladium tetrakis(triphenylphosphine) (18.46 mg, 0.016 mmol) was pumped and backfilled with nitrogen 3 times. N,N-Dimethylacetamide (2 mL) was added. The mixture was again pumped and backfilled with nitrogen 3 times. The reaction tube was sealed and heated to 150° C. under microwave for 30 min. The mixture was diluted with ethyl acetate (30 mL), washed with 1:1 mixture of brine and water (15 mL), brine (15 mL), dried (MgSO4) and concentrated. Silica gel chromatography, loading with toluene and eluting with 5-30% ethyl acetate in hexanes, gave 3-chloro-2-(4-methoxyphenyl)-5-(4-phenoxyphenyl)isonicotinonitrile (72.7 mg, 52% yield). 1H NMR (500 MHz, CDCl3) δ ppm 8.75 (1H, s), 7.74-7.83 (2H, m), 7.56-7.64 (2H, m), 7.37-7.47 (2H, m), 7.21 (1H, t, J=7.42 Hz), 7.09-7.18 (4H, m), 7.00-7.09 (2H, m), 3.90 (3H, s); MS (ES+) m/z: 413 (M+H); LC retention time: 4.810 min (analytical HPLC Method A).

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