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Ethyl 4-methyl-1H-pyrrole-2-carboxylate → 1-[2-(1-tert-butyl-1H-pyrazol-4-yl)-2-oxo-ethyl]-4-methyl-1H-pyrrole-2-carboxylic acid ethyl ester

HRID 2272972
ノート
印刷プレビュー

反応式

HRID 2272972 の反応式
[CH2:1]([O:3][C:4]([C:6]1[NH:7][CH:8]=[C:9]([CH3:11])[CH:10]=1)=[O:5])[CH3:2].[K].CC(C)([O-])C.Br[CH2:19][C:20]([C:22]1[CH:23]=[N:24][N:25]([C:27]([CH3:30])([CH3:29])[CH3:28])[CH:26]=1)=[O:21]>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:19][C:20]([C:22]2[CH:23]=[N:24][N:25]([C:27]([CH3:30])([CH3:29])[CH3:28])[CH:26]=2)=[O:21])[CH:8]=[C:9]([CH3:11])[CH:10]=1)=[O:5])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 643361Ethyl 4-methyl-1H-pyrrole-2-carboxylateHCID 50987170Potassium tertbutoxideHCID 898260822-bromo-1-(1-tert-butyl-1H-pyrazol-4-yl)-ethanone

生成物 1

HCID 898261431-[2-(1-tert-butyl-1H-pyrazol-4-yl)-2-oxo-ethyl]-4-methyl-1H-pyrrole-2-carboxylic acid ethyl ester

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a suspension of 229 mg (1.50 mmol) 4-methyl-1H-pyrrole-2-carboxylic acid ethyl ester in 3.7 ml DMF is added 185 mg (1.65 mmol) potassium-tertbutoxide portionwise under nitrogen. The mixture is stirred for 30 minutes at room temperature and cooled to 0° C. Then 367 mg (1.50 mmol) 2-bromo-1-(1-tert-butyl-1H-pyrazol-4-yl)-ethanone is added. The mixture is stirred for 1 hour at 0° C. and for 30 minutes at room temperature. The reaction mixture is partitioned between dichloromethane and water. The organic phase is dried over sodium sulfate and evaporated. The residue is chromatographed on a silica gel column with cyclohexane/ethyl acetate to afford 1-[2-(1-tert-butyl-1H-pyrazol-4-yl)-2-oxo-ethyl]-4-methyl-1H-pyrrole-2-carboxylic acid ethyl ester as yellow oil; HPLC/MS 2.82 min (B), [M+H] 318.

後処理

  1. temperaturecooled to 0° C
  2. stirringThe mixture is stirred for 1 hour at 0° C. and for 30 minutes at room temperature
  3. customThe reaction mixture is partitioned between dichloromethane and water
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. customevaporated
  6. customThe residue is chromatographed on a silica gel column with cyclohexane/ethyl acetate

出典と根拠

ORDレコード
ord-e6d361df7c904b3282ccacbc6c844387
出典データセット
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09120805B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート