Cesium carbonate → tert-butyl 5-(2-oxopyrrolidin-1-yl)-1H-indole-1-carboxylate

HRID 1467977

반응식

HRID 1467977 반응식
I[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:6]=[CH:5]2.[NH:18]1[CH2:22][CH2:21][CH2:20][C:19]1=[O:23].C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C(Cl)(Cl)Cl.[Pd].[Pd]>[O:23]=[C:19]1[CH2:20][CH2:21][CH2:22][N:18]1[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:6]=[CH:5]2

참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 120252-PyrrolidoneHCID 161259585-Iodo-1H-indole, N-BOC protected

생성물 1

HCID 67616327tert-butyl 5-(2-oxopyrrolidin-1-yl)-1H-indole-1-carboxylate수율 61.9%

시약·촉매·용매 2

HCID 11029508Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)촉매HCID 312751,4-Dioxane용매

실험 절차

To a stirred mixture of tert-butyl 5-iodo-1H-indole-1-carboxylate (1.5 g, 4.3 mmol), Xant Phos (0.25 g, 0.43 mmol) and 2-pyrrolidinone (0.74 g, 8.7 mmol) in anhydrous dioxane (15 mL), cesium carbonate (2.8 g, 8.7 mmol) was added and the contents were stirred for 5 minutes. Tris(dibenzylideneacetone)-dipalladium (0)chloroform adduct (0.452 g, 0.437 mmol) was added and the reaction mixture was stirred at 110-115° C. for 6 h. The reaction mixture was cooled to room temperature and filtered over celite and filtrate was extracted with ethyl acetate. The organic layer was concentrated in vacuo and the residue was purified by flash column chromatography to yield tert-butyl 5-(2-oxopyrrolidin-1-yl)-1H-indole-1-carboxylate (0.80 g, 61%); MS: 301 (M+1).

후처리

  1. additionwas added
  2. stirringthe reaction mixture was stirred at 110-115° C. for 6 h
  3. filtrationfiltered over celite and filtrate
  4. extractionwas extracted with ethyl acetate
  5. concentrationThe organic layer was concentrated in vacuo
  6. customthe residue was purified by flash column chromatography

출처 및 근거

ORD 기록
ord-c76cba1980ce4fd093d34909079f1882
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09000175B2

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