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

HRID 1487486Notes

Reaction equation

HRID 1487486 reaction equation
[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]

Participants

5

Reactant 2

HCID 66144Ethyl bromopyruvateHCID 6932822-Amino-4-bromopyridine

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
115 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-a561afbacdd946069bfb10a0cf0f9261
Source dataset
uspto-grants-2016_08
Patent number
US09428528B2

Reaction notes

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