Oxazole → HCID 68816107、化合物

HRID 732492

反応式

HRID 732492 の反応式
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

参加物

8

反応物 3

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

生成物 1

HCID 68816107HCID 68816107、化合物収率 82%

試薬・触媒・溶媒 4

HCID 3007855Zincchloride触媒HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-212d4cacf3a84ebda025b0d1763030c4
出典データセット
uspto-grants-2009_09
特許番号
US07585885B2

関連ノート

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