Ethyl 2-aminobenzoate → Ethyl acetate hexane

HRID 42070

反応式

HRID 42070 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[CH:9]=2)=[N:6][CH:7]=1.[NH2:16][C:17]1[CH:27]=[CH:26][CH:25]=[CH:24][C:18]=1[C:19]([O:21][CH2:22][CH3:23])=[O:20].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.CC([O-])(C)C.[Na+]>C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:7][CH2:2][CH2:3][CH2:4][CH2:5][CH3:8].[C:19]([O:21][CH2:22][CH3:23])(=[O:20])[CH3:18].[CH3:15][O:14][C:10]1[CH:9]=[C:8]([C:5]2[N:6]=[CH:7][C:2]([NH:16][C:17]3[CH:27]=[CH:26][CH:25]=[CH:24][C:18]=3[C:19]([OH:21])=[O:20])=[CH:3][CH:4]=2)[CH:13]=[CH:12][CH:11]=1

参加物

8

反応物 4

HCID 6877Ethyl 2-aminobenzoate2 回HCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxideHCID 497585195-Bromo-2-(3-methoxyphenyl)pyridine2 回

生成物 2

HCID 21226206Ethyl acetate hexane収率 98.4%HCID 251869992-(6-(3-Methoxyphenyl)pyridin-3-ylamino)benzoic acid

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 1140Toluene溶媒

反応条件

温度
110 °C

実験手順

In a schlenck tube, a mixture of 5-bromo-2-(3-methoxyphenyl)pyridine (Intermediate 27, 0.91 mmol, 0.23 g), ethyl 2-aminobenzoate (Intermediate 33, 0.91 mmol, 0.15 g), BINAP (0.05 mmol, 0.028 g), Pd2(dba)3 (0.05 mmol, 0.042 g) and NaOtBu (1.82 mmol, 0.175 g) in toluene (4 ml) was heated at 110° C. for 12 hours, under argon atmosphere. The solvent was evaporated and the solid residue was triturated with aqueous solution of 2N HCl and extracted with CHCl3. The crude mixture was purified by flash chromatography over SiO2 eluting with mixtures of hexane/ethyl acetate affording 0.078 g (yield 26%) of the expected compound.

後処理

  1. customThe solvent was evaporated
  2. customthe solid residue was triturated with aqueous solution of 2N HCl
  3. extractionextracted with CHCl3

出典と根拠

ORDレコード
ord-0c6010783c884be28f919b4217d37301
出典データセット
uspto-grants-2013_09
特許番号
US08536165B2

関連ノート

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