Cesium carbonate → (R/S)-Ethyl 2-(7-(Cyclopentyl-3-(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetate

HRID 62805

반응식

HRID 62805 반응식
[OH:1][C:2]1[CH:10]=[CH:9][C:8]2[NH:7][C:6]3[CH:11]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:12][CH2:13][C:5]=3[C:4]=2[CH:3]=1.ClC[C:22]1[CH:27]=[CH:26][C:25]([CH:28]2[CH2:32][CH2:31][CH2:30][CH2:29]2)=[C:24]([C:33]([F:36])([F:35])[F:34])[CH:23]=1.[C:37](=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH:28]1([CH:25]([O:1][C:2]2[CH:10]=[CH:9][C:8]3[NH:7][C:6]4[CH:11]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:12][CH2:13][C:5]=4[C:4]=3[CH:3]=2)[C:26]2[CH:27]=[CH:22][CH:23]=[C:24]([C:33]([F:34])([F:35])[F:36])[CH:37]=2)[CH2:29][CH2:30][CH2:31][CH2:32]1

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 53345675Ethyl 2-(7-hydroxy-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetateHCID 534026024-(Chloromethyl)-1-cyclopentyl-2-(trifluoromethyl)benzene

생성물 1

HCID 131737200(R/S)-Ethyl 2-(7-(Cyclopentyl-3-(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetate수율 41.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of ethyl 2-(7-hydroxy-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetate (50.0 mg, 0.193 mmol) and 4-(chloromethyl)-1-cyclopentyl-2-(trifluoromethyl)benzene (152.0 mg, 0.578 mmol) in DMF (3 mL) was added cesium carbonate (75.0 mg, 0.231 mmol). The mixture was stirred at room temperature overnight, filtered through Celite®, and concentrated under reduced pressure. The residue was purified by HPLC to give the title compound as a light pink oil (38.7 mg). LCMS m/z=486.5 [M+H]+.

후처리

  1. filtrationfiltered through Celite®
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by HPLC

출처 및 근거

ORD 기록
ord-630219a065ec49309e23dc6be3a6dec8
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447041B2

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