Acetic Acid → HCID 58154281, 화합물

HRID 1619102노트

반응식

HRID 1619102 반응식
C(=O)([O-])[O-].[Cs+].[Cs+].[Br:7][C:8]1[CH:16]=[C:15]2[C:11]([CH2:12][C:13](=[O:24])[N:14]2[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[CH:10][CH:9]=1.I[CH2:26][CH2:27][O:28][CH2:29][CH2:30]I.C(O)(=O)C>CN(C=O)C.O.C(OCC)(=O)C>[Br:7][C:8]1[CH:16]=[C:15]2[N:14]([C:17]([O:19][C:20]([CH3:21])([CH3:23])[CH3:22])=[O:18])[C:13](=[O:24])[C:12]3([CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)[C:11]2=[CH:10][CH:9]=1

참가 물질

8

반응물 4

HCID 176Acetic AcidHCID 10796Cesium carbonateHCID 34307791-Iodo-2-(2-iodoethoxy)ethaneHCID 58154275Tert-butyl 6-bromo-2-oxoindoline-1-carboxylate

생성물 1

HCID 58154281HCID 58154281, 화합물수율 73.6%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

Cesium carbonate (20.7 g, 63.5 mmol) was added portionwise over a 20 minute period to a stirred solution of tert-butyl 6-bromo-2-oxoindoline-1-carboxylate (preparation 8a, 6.0 g, 16.0 mmol) and 1-iodo-2-(2-iodoethoxy)ethane (6.58 g, 17.6 mmol) in N,N′-dimethylformamide (250 mL) at −20° C. under an argon atmosphere. After the addition the mixture was warmed to room temperature and stirred for 3 hours. Acetic acid (1.1 mL) followed by ethyl acetate and water were added to the reaction mixture and the organic layer was separated, washed with water, dried (MgSO4) and evaporated. Purification of the residue by flash chromatography (10:1 to 5:1 hexanes/ethyl acetate) gave the title compound (4.50 g, 61%) as a pale yellow solid.

후처리

  1. additionAfter the addition the mixture
  2. additionwere added to the reaction mixture
  3. customthe organic layer was separated
  4. washwashed with water
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customPurification of the residue by flash chromatography (10:1 to 5:1 hexanes/ethyl acetate)

출처 및 근거

ORD 기록
ord-36f2481eb1d040969945856d40836e72
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08772288B2

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