2-Aminopyridine → Methyl 3-methylimidazo[1,2-a]pyridine-2-carboxylate

HRID 1798714노트

반응식

HRID 1798714 반응식
Br[CH:2]([CH3:9])[C:3](=O)[C:4]([O:6][CH3:7])=[O:5].[NH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1>C(#N)C>[CH3:9][C:2]1[N:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]2=[N:10][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

참가 물질

4

반응물 2

HCID 104392-AminopyridineHCID 11183175Methyl 3-bromo-2-oxobutanoate

생성물 1

HCID 57690029Methyl 3-methylimidazo[1,2-a]pyridine-2-carboxylate수율 30.7%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

Methyl 3-bromo-2-oxobutanoate (6.5 g, 34.3 mmol) was added to a stirred solution of 2-aminopyridine (4.0 g, 42.5 mmol) in acetonitrile (100 ml). The mixture was heated at reflux for 14 h (the reaction was monitored by TLC). The mixture was concentrated in vacuo and the residue was diluted with water and the pH was to 7.5 using sodium bicarbonate solution. The mixture was extracted with EtOAc; the combined organics were dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography using 8% ethyl acetate in n-hexane and silica gel (230-400 mesh) to afford methyl 3-methylimidazo[1,2-a]pyridine-2-carboxylate (2.0 g, 25.1%) as a pale yellow solid. 1H NMR: 200 MHz, CDCl3: δ 7.95 (d, 1H), 7.7 (d, 1H), 7.25 (t, 1H), 6.8 (t, 1H), 4.0 (s, 3H), 2.8 (s, 3H). MS: [M+H]+: m/z=191.1.

후처리

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 14 h (the reaction
  3. concentrationThe mixture was concentrated in vacuo
  4. additionthe residue was diluted with water
  5. extractionThe mixture was extracted with EtOAc
  6. dry with materialthe combined organics were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by flash column chromatography

출처 및 근거

ORD 기록
ord-f240631c62f7479589282c7522edc3bd
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08343973B2

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