Diisopropylamine → HCID 66699464, 화합물

HRID 1096039노트

반응식

HRID 1096039 반응식
[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

참가 물질

8

반응물 5

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

생성물 1

HCID 66699464HCID 66699464, 화합물

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-78 °C

실험 절차

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+].

후처리

  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)

출처 및 근거

ORD 기록
ord-17615b22984a4cfc84b1a85c614357de
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08138189B2

반응 노트

불러오는 중…