Ethyl (chloroformyl)acetate → Ethyl 7-iodo-6-methylimidazo[1,2-a]pyridine-3-carboxylate

HRID 1748199노트

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HRID 1748199 반응식
[I:1][C:2]1[C:7]([CH3:8])=[CH:6][N:5]=[C:4]([NH2:9])[CH:3]=1.C(=O)(O)[O-].[Na+].Cl[CH:16]([CH:22]=O)[C:17]([O:19][CH2:20][CH3:21])=[O:18]>C(COC)OC.ClCCl>[I:1][C:2]1[C:7]([CH3:8])=[CH:6][N:5]2[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:22][N:9]=[C:4]2[CH:3]=1

참가 물질

6

반응물 3

HCID 118030Ethyl (chloroformyl)acetateHCID 516892Sodium BicarbonateHCID 667478634-Iodo-5-methylpyridin-2-amine

생성물 1

HCID 67985150Ethyl 7-iodo-6-methylimidazo[1,2-a]pyridine-3-carboxylate

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 80711,2-Dimethoxyethane용매2회

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온도
100 °C

실험 절차

To a suspension of 4-iodo-5-methylpyridin-2-amine (I-28A) (1.55 g. 6.6 mmol), sodium bicarbonate (0.67 g, 7.9 mmol) in dry dimethoxyethane (10 mL) at room temperature, ethyl 2-chloro-3-oxopropanoate (1 g, 6.41 mmol) in dimethoxyethane (1 mL) was added dropwise. The reaction mixture was heated to 100° C. for 1 h and then cooled to room temperature and diluted with dichloromethane (50 mL). The organic layer was washed with water, brine, dried over sodium sulfate and concentrated in vacuo. The brown crude oil was purified by silica gel chromatography with a gradient of 0-15% ethyl acetate/hexanes to yield ethyl 7-iodo-6-methylimidazo[1,2-a]pyridine-3-carboxylate (I-28B) as light tan solid. 1H-NMR (400 MHz, DMSO) δ 9.11 (s, 1H), 8.41 (s, 1H), 8.22 (s, 1H), 4.36 (q, J=7.2 Hz, 2H), 2.42 (s, 3H), 1.37 (t, J=7.2 Hz, 3H). MS m/z 331.0 (M+1).

후처리

  1. temperaturecooled to room temperature
  2. washThe organic layer was washed with water, brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe brown crude oil was purified by silica gel chromatography with a gradient of 0-15% ethyl acetate/hexanes

출처 및 근거

ORD 기록
ord-5549f69cc4a043b0b40e6aa6599c2f50
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09150568B2

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