Cesium carbonate → Ethyl 2-(2-(3-Cyano-5-(trifluoromethoxy)benzyloxy)-6,7,8,9-tetrahydropyrido[1,2-a]indol-9-yl)acetate

HRID 1964167

반응식

HRID 1964167 반응식
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]1[CH2:11][CH2:12][CH2:13][CH:14]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:6]1=[CH:5]2.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[CH2:28][C:29]1[CH:30]=[C:31]([CH:34]=[C:35]([O:37][C:38]([F:41])([F:40])[F:39])[CH:36]=1)[C:32]#[N:33]>CN(C=O)C>[C:32]([C:31]1[CH:30]=[C:29]([CH:36]=[C:35]([O:37][C:38]([F:39])([F:41])[F:40])[CH:34]=1)[CH2:28][O:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]1[CH2:11][CH2:12][CH2:13][CH:14]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:6]1=[CH:5]2)#[N:33]

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 668477373-(Chloromethyl)-5-(trifluoromethoxy)benzonitrileHCID 67249257Ethyl 2-(2-hydroxy-6,7,8,9-tetrahydropyrido[1,2-a]indol-9-yl)acetate

생성물 1

HCID 67248872Ethyl 2-(2-(3-Cyano-5-(trifluoromethoxy)benzyloxy)-6,7,8,9-tetrahydropyrido[1,2-a]indol-9-yl)acetate수율 83.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
75 °C

실험 절차

To a mixture of ethyl 2-(2-hydroxy-6,7,8,9-tetrahydropyrido[1,2-a]indol-9-yl)acetate (75 mg, 0.274 mmol) and cesium carbonate (134 mg, 0.412 mmol) in DMF (2 mL) was added 3-(chloromethyl)-5-(trifluoromethoxy)benzonitrile (78 mg, 0.329 mmol). The reaction was heated at 75° C. for 15 h and cooled down. The solid was filtered and washed with ethyl acetate. The combined solvent was evaporated, and the residue was purified by silica gel column chromatography to give the title compound (108 mg). LCMS m/z=473.6 [M+H]+; 1H NMR (400 MHz, CDCl3) δ ppm 1.30 (t, J=7.1 Hz, 3H), 1.51-1.62 (m, 1H), 2.00-2.10 (m, 1H), 2.10-2.24 (m, 2H), 2.55 (dd, J=15.6, 8.6 Hz, 1H), 2.93 (dd, J=15.6, 5.5 Hz, 1H), 3.45-3.54 (m, 1H), 3.85-3.93 (m, 1H), 4.10-4.17 (m, 1H), 4.22 (q, J=7.1 Hz, 2H), 5.14 (s, 2H), 6.18 (s, 1H), 6.87 (dd, J=8.8, 2.4 Hz, 1H), 7.05 (d, J=2.4 Hz, 1H), 7.18 (d, J=8.8 Hz, 1H), 7.44 (s, 1H), 7.58 (s, 1H), 7.71 (s, 1H).

후처리

  1. temperaturecooled down
  2. filtrationThe solid was filtered
  3. washwashed with ethyl acetate
  4. customThe combined solvent was evaporated
  5. customthe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-900c8d887e794875b44ef4b1b36586f7
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08415484B2

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