Triethylamine → tert-butyl 3-(1-benzyl-1H-pyrazol-4-yl)-5,6-dihydropyridine-1(2H)-carboxylate

A 250-mL 3-necked round-bottomed flask was charged with a solution of tert-butyl 3-(trifluoromethylsulfonyloxy)-5,6-dihydropyridine-1(2H)-carboxylate (5.0 g, 15.11 mmol, 1.00 equiv) in toluene (100 mL), a solution of 1-benzyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (4.29 g, 15.11 mmol, 1.00 equiv) in ethanol (100 mL), triethylamine (4.58 g, 45.35 mmol, 3.00 equiv), Pd(PPh3)4 (345 mg, 0.30 mmol, 0.01 equiv) and water (30 mL). The resulting mixture was heated to reflux for 3 hours. Upon completion, the mixture was diluted with water (100 mL). Then, it was extracted with ethyl acetate (3×200 mL). Combined organic layers were dried over anhydrous sodium sulfate and concentrated on a rotary evaporator. The residue was purified by silica gel column chromatography eluted with ethyl acetate/petroleum ether (1:5) affording tert-butyl 3-(1-benzyl-1H-pyrazol-4-yl)-5,6-dihydropyridine-1(2H)-carboxylate as yellow oil (5.0 g, 98%).

1. temperatureThe resulting mixture was heated
2. temperatureto reflux for 3 hours
3. extractionThen, it was extracted with ethyl acetate (3×200 mL)
4. dry with materialCombined organic layers were dried over anhydrous sodium sulfate
5. concentrationconcentrated on a rotary evaporator
6. customThe residue was purified by silica gel column chromatography
7. washeluted with ethyl acetate/petroleum ether (1:5)

ORDレコード

ord-b8d32d5b00974c9288c4fc6f138fa45e

出典データセット

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08080566B1