Ethyl 2-aminobenzoate → Ethyl acetate hexane

HRID 42070

반응식

HRID 42070 반응식
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

참가 물질

8

반응물 4

HCID 6877Ethyl 2-aminobenzoate2회HCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxideHCID 497585195-Bromo-2-(3-methoxyphenyl)pyridine2회

생성물 2

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

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매

반응 조건

온도
110 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-0c6010783c884be28f919b4217d37301
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536165B2

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