N-bromobutanimide → Ethyl 6-bromopyrrolo[1,2-a]pyrazine-3-carboxylate

HRID 25161Notes

Reaction equation

HRID 25161 reaction equation
[CH:1]1[C:2]2[N:3]([CH:12]=[CH:13][CH:14]=2)[CH:4]=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:6]=1.[Br:15]N1C(=O)CCC1=O>C(Cl)Cl>[Br:15][C:12]1[N:3]2[CH:4]=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:6]=[CH:1][C:2]2=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 22566021Ethyl pyrrolo[1,2-a]pyrazine-3-carboxylate

Product 1

HCID 22565747Ethyl 6-bromopyrrolo[1,2-a]pyrazine-3-carboxylateYield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl pyrrolo[1,2-a]pyrazine-3-carboxylate (0.60 g, 3.18 mmol) in CH2Cl2 (60 mL) is added N-bromosuccinimide (0.56 g, 3.18 mmol) in one portion. After 1 h, solvent is removed in vacuo and the crude solid purified using preparative HPLC (1% IPA/heptane (0-5 minutes) to 2% isocratic) to give a brown solid for ethyl 6-bromopyrrolo[1,2-a]pyrazine-3-carboxylate. Yield 57%. MS (ESI+) for C10H9BrN2O2 m/z 271.01 (M+H)+.

Workup

  1. customsolvent is removed in vacuo
  2. customthe crude solid purified
  3. customHPLC (1% IPA/heptane (0-5 minutes) to 2% isocratic)

Sources & evidence

ORD record
ord-b27df28b5c5c442e933df3563681376d
Source dataset
uspto-grants-2005_02
Patent number
US06858613B2

Reaction notes

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