Ethyl Acetoacetate → Ethyl 4-amino-3,6-dimethylthieno[2,3-b]pyridine-5-carboxylate

HRID 573555노트

반응식

HRID 573555 반응식
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH3:9])[C:6]=1[C:7]#[N:8].[C:10]([O:16][CH2:17][CH3:18])(=[O:15])[CH2:11][C:12]([CH3:14])=O.Cl[Sn](Cl)(Cl)Cl>C1(C)C=CC=CC=1>[NH2:8][C:7]1[C:11]([C:10]([O:16][CH2:17][CH3:18])=[O:15])=[C:12]([CH3:14])[N:1]=[C:2]2[S:3][CH:4]=[C:5]([CH3:9])[C:6]=12

참가 물질

5

반응물 3

HCID 8868Ethyl AcetoacetateHCID 24287Tin tetrachlorideHCID 2642812-Amino-4-methylthiophene-3-carbonitrile

생성물 1

HCID 68323726Ethyl 4-amino-3,6-dimethylthieno[2,3-b]pyridine-5-carboxylate수율 38.6%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

A mixture of 2-amino-4-methyl-3-thiophenecarbonitrile (300 mg, 2.171 mmol), ethyl acetoacetate (0.275 mL, 2.171 mmol) and SnCl4 (0.510 mL, 434 mmol) in toluene (15 mL) was stirred at RT for 30 min and then reflux for 3.5 h. After cooling to RT, the mixture was quenched with 6M NaOH (20 mL) and extracted with ethyl acetate (3×20 mL). The combined organics were washed with brine (30 mL), dried and concentrated. Purification by chromatography on silica gel, eluting with a gradient of 0-50% ethyl acetate in cyclohexane, afforded the title compound (210 mg). LCMS (A) m/z: 251 [M+1]+, Rt 0.77 min (acidic).

후처리

  1. temperaturereflux for 3.5 h
  2. temperatureAfter cooling to RT
  3. customthe mixture was quenched with 6M NaOH (20 mL)
  4. extractionextracted with ethyl acetate (3×20 mL)
  5. washThe combined organics were washed with brine (30 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-4c4c5f8993c744e5b8256fcc68aa764b
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09029545B2

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