Diisopropylamine → HCID 57722998, 화합물

HRID 1987034노트

반응식

HRID 1987034 반응식
C([Li])CCC.C(NC(C)C)(C)C.[C:13]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])(=[O:15])[CH3:14].Br[CH2:22][C:23]1[C:24]([Cl:37])=[N:25][C:26]([Cl:36])=[CH:27][C:28]=1[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[Cl:35]>C1COCC1.[Cl-].[Na+].O.C(OCC)(=O)C.C(O)(=O)C>[Cl:37][C:24]1[C:23]([CH2:22][CH2:14][C:13]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[C:28]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[Cl:35])[CH:27]=[C:26]([Cl:36])[N:25]=1

참가 물질

9

반응물 4

HCID 7912DiisopropylamineHCID 10908tert-Butyl acetateHCID 57722989HCID 57722989, 화합물HCID 178418339Butyllithium

생성물 1

HCID 57722998HCID 57722998, 화합물수율 91%

시약·촉매·용매 4

HCID 176Acetic Acid용매HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매HCID 57417360Sodium chloride; water용매

실험 절차

n-Butyllithium in hexanes (1.6M, 18 ml, 28.8 mmol) was added to di-isopropylamine (4.1 ml, 29.25 mmol) in dry THF (200 ml) at −10° under nitrogen. After 5 min. the solution was cooled to −70° and tert-butyl acetate (3.9 ml, 28.93 mmol) added dropwise. After stirring at −70° for 15 min. under nitrogen, 3-(bromomethyl)-2,6-dichloro-4-(2-chlorophenyl)pyridine (2.44 g, 6.942 mmol) in dry THF (18 ml) was added dropwise over 10 min., and the mixture stirred at −70° for 1 h. Glacial acetic acid (2.3 ml) was added, the temperature allowed to rise to 22° and brine (200 ml) and ethyl acetate (100 ml) added. The phases were separated and the aqueous further extracted with ethyl acetate (150 ml). The extracts were dried (Na2SO4), evaporated in vacuo and the residue purified by flash chromatography over silica eluting with cyclohexane-ethyl acetate (100:0-50:50) to give the title compound as a viscous gum (2.44 g, 91%).

후처리

  1. temperatureAfter 5 min. the solution was cooled to −70°
  2. stirringthe mixture stirred at −70° for 1 h
  3. customto rise to 22°
  4. customThe phases were separated
  5. extractionthe aqueous further extracted with ethyl acetate (150 ml)
  6. dry with materialThe extracts were dried (Na2SO4)
  7. customevaporated in vacuo
  8. customthe residue purified by flash chromatography over silica eluting with cyclohexane-ethyl acetate (100:0-50:50)

출처 및 근거

ORD 기록
ord-01837af03117470189c77db87251c528
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07550480B2

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