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Ethyl bromopyruvate → Ethyl 7-bromoimidazo(1,2-a)pyridine-2-carboxylate

HRID 1487486
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HRID 1487486 반응식
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH2:8])[CH:3]=1.[CH2:9]([O:11][C:12](=[O:17])[C:13](=O)[CH2:14]Br)[CH3:10]>C1(C)C=CC=CC=1.O>[CH2:9]([O:11][C:12]([C:13]1[N:8]=[C:4]2[CH:3]=[C:2]([Br:1])[CH:7]=[CH:6][N:5]2[CH:14]=1)=[O:17])[CH3:10]
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참가 물질

5

반응물 2

HCID 66144Ethyl bromopyruvateHCID 6932822-Amino-4-bromopyridine

생성물 1

HCID 51063904Ethyl 7-bromoimidazo(1,2-a)pyridine-2-carboxylate수율 104.5%

시약·촉매·용매 2

HCID 962Water용매HCID 1140Toluene용매

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온도
115 °C

실험 절차

To a stirred solution of 4-Bromo-pyridin-2-ylamine (4 g, 23.12 mmol) in toluene (40 mL) is added 3-Bromo-2-oxo-propionic acid ethyl ester (4.5 g, 23.12 mmol). The reaction mixture is heated at 115° C. for 16 hours. Reaction mixture is cooled to 0° C. then diluted with water and extract with ethyl acetate. Organic layer is dried over sodium sulphate, solvent is evaporated in vacuo to afford the title compound (6.5 g). 1H-NMR (400 MHz, DMSO-d6) δ: 1.31 (t, J=7.2 Hz, 3H), 4.26-4.33 (q, J=7.2 Hz, 2H), 7.18-7.20 (dd, J1=1.92 Hz, J2=7.16 Hz, 1H), 7.98 (s, 1H), 8.53 (d, J=7.32 Hz, 1H), 8.57 (s, 1H). LC-MS (m/z): [M+H]=271.0.

후처리

  1. customReaction mixture
  2. temperatureis cooled to 0° C.
  3. extractionextract with ethyl acetate
  4. dry with materialOrganic layer is dried over sodium sulphate, solvent
  5. customis evaporated in vacuo

출처 및 근거

ORD 기록
ord-a561afbacdd946069bfb10a0cf0f9261
출처 데이터셋
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09428528B2

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