Acetonitrile → 1-({5-[3,5-Bis(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl}methyl)-2-propyl-4-(trifluoromethyl)-1H-indole-5-carbonitrile

HRID 1188469

반응식

HRID 1188469 반응식
[CH2:1]([C:4]1[NH:5][C:6]2[C:11]([CH:12]=1)=[C:10]([C:13]([F:16])([F:15])[F:14])[C:9]([C:17]#[N:18])=[CH:8][CH:7]=2)[CH2:2][CH3:3].[F:19][C:20]([F:39])([F:38])[C:21]1[CH:22]=[C:23]([C:31]2[O:35][N:34]=[C:33]([CH2:36]Cl)[N:32]=2)[CH:24]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:26]=1.C([O-])([O-])=O.[Cs+].[Cs+].CC#N>CCOC(C)=O>[F:39][C:20]([F:19])([F:38])[C:21]1[CH:22]=[C:23]([C:31]2[O:35][N:34]=[C:33]([CH2:36][N:5]3[C:6]4[C:11](=[C:10]([C:13]([F:15])([F:16])[F:14])[C:9]([C:17]#[N:18])=[CH:8][CH:7]=4)[CH:12]=[C:4]3[CH2:1][CH2:2][CH3:3])[N:32]=2)[CH:24]=[C:25]([C:27]([F:29])([F:28])[F:30])[CH:26]=1

참가 물질

6

반응물 4

HCID 6342AcetonitrileHCID 10796Cesium carbonateHCID 27809575-[3,5-Bis(trifluoromethyl)phenyl]-3-(chloromethyl)-1,2,4-oxadiazoleHCID 674051552-propyl-4-(trifluoromethyl)-1H-indole-5-carbonitrile

생성물 1

HCID 866206731-({5-[3,5-Bis(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl}methyl)-2-propyl-4-(trifluoromethyl)-1H-indole-5-carbonitrile수율 81%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

반응 조건

온도
75 °C

실험 절차

A mixture of 2-propyl-4-(trifluoromethyl)-1H-indole-5-carbonitrile (0.040 g, 0.16 mmol), 5-[3,5-bis(trifluoromethyl)phenyl]-3-(chloromethyl)-1,2,4-oxadiazole (0.058 g, 0.17 mmol), Cs2CO3 (0.057 g, 0.17 mmol) and CH3CN (4 mL) was stirred at 75° C. for 1.5 h. The mixture was diluted with EtOAc (25 mL), washed with water (15 mL), and brine (15 mL). The organic portion was dried (MgSO4), filtered, and concentrated. The concentrated material was treated with 10% Et2O in hexanes (10 mL) and stirred for 2 h. The resulting solid was filtered, rinsed with hexanes, and dried to afford the title compound (0.070 g, 81%) as a light tan solid: 1H NMR (400 MHz, DMSO-d6) δ 8.53 (s, 2H), 8.50 (s, 1H), 8.03 (d, J=8.6 Hz, 1H), 7.75 (d, J=8.6 Hz, 1H), 6.59 (s, 1H), 5.90 (s, 2H), 2.90 (t, J=7.5 Hz, 2H), 1.79-1.70 (m, 2H), 0.98 (t, J=7.4 Hz, 3H); MS m/z 547 (M+H).

후처리

  1. washwashed with water (15 mL), and brine (15 mL)
  2. dry with materialThe organic portion was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. additionThe concentrated material was treated with 10% Et2O in hexanes (10 mL)
  6. stirringstirred for 2 h
  7. filtrationThe resulting solid was filtered
  8. washrinsed with hexanes
  9. customdried

출처 및 근거

ORD 기록
ord-4e221fbf794c4942912e617d60e98ea3
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08673948B2

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