Acetic Acid → HCID 58154281、化合物

HRID 1619102ノート

反応式

HRID 1619102 の反応式
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

参加物

8

反応物 4

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

生成物 1

HCID 58154281HCID 58154281、化合物収率 73.6%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-36f2481eb1d040969945856d40836e72
出典データセット
uspto-grants-2014_07
特許番号
US08772288B2

反応ノート

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