Water → HCID 44136066, compound

HRID 2363730Notes

Reaction equation

HRID 2363730 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[CH:8][C:9]2[N:10]([CH:12]=[C:13]([C:15]([NH:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:16])[N:14]=2)[CH:11]=1)=[CH2:5])C.O.[Br:25]N1C(=O)CCC1=O>O1CCCC1.ClCCl>[Br:25][CH2:3][C:4]([C:6]1[CH:7]=[CH:8][C:9]2[N:10]([CH:12]=[C:13]([C:15]([NH:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:16])[N:14]=2)[CH:11]=1)=[O:5]

Participants

6

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 44136067HCID 44136067, compound

Product 1

HCID 44136066HCID 44136066, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 123 mg of 6-(1-ethoxyvinyl)-N-phenylimidazo[1,2-a]pyridine-2-carboxamide in 4 mL of tetrahydrofuran are added 1 mL of water and then, after cooling to 0° C., 71 mg of N-bromosuccinimide. The reaction mixture is stirred for 2.5 hours at room temperature and then diluted with 80 mL of dichloromethane. The organic phase is washed with water and then dried and concentrated to dryness under reduced pressure to give 60 mg of crude 6-(2-bromoacetyl)-N-phenylimidazo[1,2-a]pyridine-2-carboxamide in the form of a white solid (containing small amounts of 6-acetyl derivative and dibromo derivative) that is used without further purification.

Workup

  1. washThe organic phase is washed with water
  2. customdried
  3. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-4f5e04776f2a47678825e88ccf429193
Source dataset
uspto-grants-2014_04
Patent number
US08691990B2

Reaction notes

Loading…