N-bromobutanimide → HCID 70819495, compound

HRID 591043Notes

Reaction equation

HRID 591043 reaction equation
[C:1]([O:5][CH:6]([C:11]1[N:12]=[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]2[CH:19]=1)[C:7]([O:9][CH3:10])=[O:8])([CH3:4])([CH3:3])[CH3:2].[Br:20]N1C(=O)CCC1=O>C(O)C>[Br:20][C:19]1[N:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]2=[N:12][C:11]=1[CH:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])[C:7]([O:9][CH3:10])=[O:8]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 70819501HCID 70819501, compound

Product 1

HCID 70819495HCID 70819495, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of methyl 2-(tert-butoxy)-2-{imidazo[1,2-a]pyridin-2-yl}acetate (25c) (108 mg, 0.41 mmol) in ethanol (5 mL) at 0° C. was added N-bromosuccinimide (76 mg, 0.43 mmol) portionwise. The mixture was stirred at 0° C. for 15 minutes and concentrated in vacuo. The residue was dissolved in ethyl acetate (5 mL) and washed with a saturated solution of sodium hydrogencarbonate (2×5 mL). The organic layer was dried over sodium sulfate and concentrated in vacuo to provide the desired product (25d) (127 mg, 0.37 mmol, 90%) as a yellow oil which was used without further purification.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate (5 mL)
  3. washwashed with a saturated solution of sodium hydrogencarbonate (2×5 mL)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b8c0fee9572247e58b320a62185f8827
Source dataset
uspto-grants-2016_01
Patent number
US09238026B2

Reaction notes

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