Ethyl Acetoacetate → Ethyl 4-amino-6-methyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridine-5-carboxylate

HRID 573546노트

반응식

HRID 573546 반응식
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[CH:10]=2)[C:6]=1[C:7]#[N:8].[C:17]([O:23][CH2:24][CH3:25])(=[O:22])[CH2:18][C:19]([CH3:21])=O.Cl[Sn](Cl)(Cl)Cl>C1(C)C=CC=CC=1>[NH2:8][C:7]1[C:18]([C:17]([O:23][CH2:24][CH3:25])=[O:22])=[C:19]([CH3:21])[N:1]=[C:2]2[S:3][CH:4]=[C:5]([C:9]3[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[CH:10]=3)[C:6]=12

참가 물질

5

반응물 3

HCID 8868Ethyl AcetoacetateHCID 24287Tin tetrachlorideHCID 167961562-Amino-4-[3-(methyloxy)phenyl]-3-thiophenecarbonitrile

생성물 1

HCID 68323793Ethyl 4-amino-6-methyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridine-5-carboxylate수율 61.6%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

A mixture of 2-amino-4-[3-(methyloxy)phenyl]-3-thiophenecarbonitrile (1 g, 4.34 mmol) (Description 13), ethyl acetoacetate (0.550 mL, 4.34 mmol) and SnCl4 (1.019 mL, 8.68 mmol) in toluene (25 mL) was stirred at RT for 30 min followed by reflux for 3 h. After cooling to RT, the mixture was quenched with 2M NaOH (50 mL) and extracted with ethyl acetate (3×40 mL). The combined organics were washed with brine (50 mL), dried and concentrated. Purification by chromatography on silica gel, eluting with a gradient of 0-50% ethyl acetate in cyclohexane, to give the title compound (915 mg). LCMS (A) m/z: 343 [M+1]+, Rt 1.25 min (acidic).

후처리

  1. temperatureby reflux for 3 h
  2. temperatureAfter cooling to RT
  3. customthe mixture was quenched with 2M NaOH (50 mL)
  4. extractionextracted with ethyl acetate (3×40 mL)
  5. washThe combined organics were washed with brine (50 mL)
  6. customdried
  7. concentrationconcentrated
  8. customPurification by chromatography on silica gel
  9. washeluting with a gradient of 0-50% ethyl acetate in cyclohexane

출처 및 근거

ORD 기록
ord-5c4aab08a7ae4938aa1026bbf02f2d4b
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09029545B2

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