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[O:1]=[C:2]1[C:10]2([CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:16]3[CH:17]=[C:18]([CH:21]=[C:22]([F:24])[CH:23]=3)[C:19]#[N:20])[CH:8]=2)[NH:3]1.[CH2:25]([O:27][CH:28](OCC)[O:29][CH2:30][CH3:31])[CH3:26]>>[CH2:25]([O:27][CH:28]([O:29][CH2:30][CH3:31])[N:3]1[C:4]2[C:9](=[CH:8][C:7]([C:16]3[CH:17]=[C:18]([CH:21]=[C:22]([F:24])[CH:23]=3)[C:19]#[N:20])=[CH:6][CH:5]=2)[C:10]2([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]2)[C:2]1=[O:1])[CH3:26]참가 물질
실험 절차
A solution of 3-(1′,2′-dihydro-2′-oxospiro[cyclohexane-1,3′-[3H]indol]-5′-yl)-5-flurobenzonitrile (1.0 eq, 0.27 g, 0.84 mmol) in triethylorthoformate (2 mL, 12 mmol) was heated to 150° C. for 1 h. The reaction mixture was allowed to cool, the excess triethylorthoformate was removed in vacuo, and the residue was purified by flash column chromatography on silica gel (eluting with 10% EtOAc/hexane) to give the title compound (0.2 g, 56%) as a white powder, mp 146° C. 1H NMR (DMSO-d6; 400 MHz) δ 1.13 (t, 6H, J=7 Hz), 1.60–1.96 (m, 10H), 3.48 (m, 2H), 3.66 (m, 2H), 6.17 (s, 1H), 7.35 (d, 1H, J=8.3 Hz), 7.68 (dd, 1H, J=2.0, 8.3 Hz), 7.77 (ddd, 1H, J=1.3, 2.4 Hz), 7.89 (d, 1H, J=2.0 Hz), 7.92 (dt, 1H, J=2.4, 10.5 Hz), 8.08 (dd, 1H, J=1.3, 2.9 Hz). MS ((+)−EI) m/z 422 [M+]. Anal. Calcd for C25H27FN2O3: C, 71.07; H, 6.44; N, 6.63. Found: C, 70.75; H, 6.48; N, 6.52.
후처리
- temperatureto cool
- customthe excess triethylorthoformate was removed in vacuo
- customthe residue was purified by flash column chromatography on silica gel (eluting with 10% EtOAc/hexane)
출처 및 근거
- ORD 기록
- ord-bb177ac4f5ee408d9791a43cc1ab2c73
- 출처 데이터셋
- uspto-grants-2006_08
- 특허 번호
- US07084168B2
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