Diisopropylamine → HCID 66699464、化合物

HRID 1096039ノート

反応式

HRID 1096039 の反応式
[CH2:1]([Li])CCC.C(NC(C)C)(C)C.[CH3:13][C:14]1[CH:18]=[CH:17][S:16][C:15]=1[C:19]#[N:20].[Br:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][CH:29]=[O:30])=[C:24]([Cl:31])[CH:23]=1.CC(C1C=CC(Br)=CC=1Cl)=O>C1COCC1.O>[Br:21][C:22]1[CH:27]=[CH:26][C:25]([CH:28]([CH3:1])[CH:29]([C:17]2[S:16][C:15]([C:19]#[N:20])=[C:14]([CH3:13])[CH:18]=2)[OH:30])=[C:24]([Cl:31])[CH:23]=1

参加物

8

反応物 5

HCID 7912DiisopropylamineHCID 5216173-Methylthiophene-2-carbonitrileHCID 155609501-(4-Bromo-2-chlorophenyl)ethan-1-oneHCID 534036162-(4-Bromo-2-chlorophenyl)acetaldehydeHCID 178418339Butyllithium

生成物 1

HCID 66699464HCID 66699464、化合物

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

A solution of n-butyllithium (1.6M) in hexanes (0.18 ml) was added to a solution of diisopropylamine (0.212 ml) in THF (2 ml) at 0° C. The mixture was stirred for 5 min and then cooled to −78° C. 3-Methylthiophene-2-carbonitrile (184 mg, CAS Reg. No. 55406-13-8) was added at −78° C. and then stirred for 30 min. A solution of 2-(4-bromo-2-chlorophenyl)ethanone (248 mg, CAS Reg. No. 749932-89-6, prepared in analogy to Example 58, step 2, from 2-chloro-4-bromoacetophenone [CAS Reg. No. 252561-81-2]) in THF (1 ml) was added at −78° C. The mixture was stirred for 20 min, then water (0.2 ml) was added. The mixture was filtered over celite and concentrated to an oil. The residue was purified by flash chromatography (SiO2, 0 to 100% EtOAc/heptane) to give the title compound (100 mg) as a colorless oil. MS (m/e)=370.0 [M+H+].

後処理

  1. addition55406-13-8) was added at −78° C.
  2. stirringstirred for 30 min
  3. stirringThe mixture was stirred for 20 min
  4. filtrationThe mixture was filtered over celite
  5. concentrationconcentrated to an oil
  6. customThe residue was purified by flash chromatography (SiO2, 0 to 100% EtOAc/heptane)

出典と根拠

ORDレコード
ord-17615b22984a4cfc84b1a85c614357de
出典データセット
uspto-grants-2012_03
特許番号
US08138189B2

反応ノート

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