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

HRID 1467977

反応式

HRID 1467977 の反応式
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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 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)触媒HCID 312751,4-Dioxane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-c76cba1980ce4fd093d34909079f1882
出典データセット
uspto-grants-2015_04
特許番号
US09000175B2

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