1,8-Diazabicyclo(5.4.0)undec-7-ene → 3-(3-chloro-1H-pyrazol-1-yl)pyridine

3-Chloro-1-(pyridine-3-yl)-4,5-dihydro-1H-pyrazole-5-carbonitrile (0.500 g, 2.42 mmol) was stirred in N,N-dimethylformamide (6.05 mL). 1,8-Diazabicyclo[5.4.0]undec-7-ene (0.543 mL, 3.63 mmol) was added and the dark mixture was stirred at room temperature overnight. LC/MS analysis indicated that the reaction was complete. The mixture was concentrated and the dark oil was dissolved in ethyl acetate and washed with 15% aqueous lithium chloride (LiCl) and brine. The organic portion was dried over sodium sulfate (Na2SO4) and concentrated. The residue was purified by flash column chromatography using ethyl acetate. The pure fractions were concentrated and the residue was vacuum dried at 45° C. to yield the desired product as a white solid (450 mg, 93%): mp: 66-68° C.; 1H NMR (400 MHz, CDCl3) δ 8.93 (d, J=27 Hz, 1H), 8.57 (dd, J=4.8, 1.4 Hz, 1H), 8.02 (ddd, J=8.3, 2.7, 1.5 Hz, 1H), 7.91 (d, J=2.6 Hz, 1H), 7.47-7.34 (m, 1H), 6.45 (d, J=2.6 Hz, 1H); 13C NMR (101 MHz, CDCl3) δ 148.01, 142.72, 140.12, 135.99, 128.64, 126.41, 124.01, 108.0.

1. concentrationThe mixture was concentrated
2. dissolutionthe dark oil was dissolved in ethyl acetate
3. washwashed with 15% aqueous lithium chloride (LiCl) and brine
4. dry with materialThe organic portion was dried over sodium sulfate (Na2SO4)
5. concentrationconcentrated
6. customThe residue was purified by flash column chromatography
7. concentrationThe pure fractions were concentrated
8. customdried at 45° C.

ORDレコード

ord-81eb36658d4e4276ad08b74bc6903743

出典データセット

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US09434712B2