Oxazole → HCID 68816107, 화합물

HRID 732492

반응식

HRID 732492 반응식
C([Li])CCC.[O:6]1[CH:10]=[CH:9][N:8]=[CH:7]1.[CH3:11][O:12][C:13](=[O:28])[C:14]1[CH:26]=[C:25](I)[CH:24]=[C:16]([C:17]([N:19]([CH3:23])[CH2:20][CH2:21][CH3:22])=[O:18])[CH:15]=1>C1COCC1.C(OCC)C.[Cl-].[Zn+2].[Cl-].C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:11][O:12][C:13](=[O:28])[C:14]1[CH:26]=[C:25]([C:7]2[O:6][CH:10]=[CH:9][N:8]=2)[CH:24]=[C:16]([C:17]([N:19]([CH3:23])[CH2:20][CH2:21][CH3:22])=[O:18])[CH:15]=1

참가 물질

8

반응물 3

HCID 9255OxazoleHCID 21086185Methyl 3-iodo-5-{[methyl(propyl)amino]carbonyl}benzoateHCID 178418339Butyllithium

생성물 1

HCID 68816107HCID 68816107, 화합물수율 82%

시약·촉매·용매 4

HCID 3007855Zincchloride촉매HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-78 °C

실험 절차

Add n-butyllithium (1.6 M in hexanes, 1.25 mL, 2.01 mmol) dropwise to a solution of oxazole (126 mg, 1.83 mmol) in THF (12.6 mL) at −78° C. Stir for 30 min at −78° C. and add a solution of zinc chloride (747 mg, 5.49 mmol) in diethyl ether (5.5 mL) and stir at 0° C. for 1 h. Add a solution of 5-iodo-N-methyl-N-propyl-isophthalamic acid methyl ester (330 mg, 0.91 mmol) in THF (5.1 mL) followed by tetrakis(triphenylphosphine)palladium (0) (105 mg, 0.091 mmol) and heat to reflux for 30 min. Add ethyl acetate (40 mL), wash with water (2×20 mL), dry (magnesium sulfate), concentrate and purify (silica gel chromatography, eluting with 50:50 ethyl acetate:hexane) to give the title compound (225 mg, 82%).

후처리

  1. stirringstir at 0° C. for 1 h
  2. temperatureheat
  3. temperatureto reflux for 30 min
  4. washAdd ethyl acetate (40 mL), wash with water (2×20 mL)
  5. dry with materialdry (magnesium sulfate)
  6. concentrationconcentrate
  7. custompurify
  8. wash(silica gel chromatography, eluting with 50:50 ethyl acetate:hexane)

출처 및 근거

ORD 기록
ord-212d4cacf3a84ebda025b0d1763030c4
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07585885B2

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