Bromine → Ethyl 8-(benzyloxy)-6-bromo-2-(4-fluorobenzyl)-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]-pyrazine-7-carboxylate

HRID 494084Notes

Reaction equation

HRID 494084 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:11][N:12]2[CH2:17][CH2:16][N:15]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)[C:14](=[O:26])[C:13]=12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+].[Br:37]Br>ClCCl>[CH2:1]([O:8][C:9]1[C:10]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[C:11]([Br:37])[N:12]2[CH2:17][CH2:16][N:15]([CH2:18][C:19]3[CH:20]=[CH:21][C:22]([F:25])=[CH:23][CH:24]=3)[C:14](=[O:26])[C:13]=12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 516892Sodium BicarbonateHCID 68864638Ethyl 8-(benzyloxy)-2-(4-fluorobenzyl)-1-oxo-1,2,3,4-tetrahydro-pyrrolo[1,2-a]-pyrazine-7-carboxylate

Product 1

HCID 68864116Ethyl 8-(benzyloxy)-6-bromo-2-(4-fluorobenzyl)-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]-pyrazine-7-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of ethyl 8-(benzyloxy)-2-(4-fluorobenzyl)-1-oxo-1,2,3,4-tetrahydro-pyrrolo[1,2-a]-pyrazine-7-carboxylate (8.0 g, 18.9 mmol) and sodium bicarbonate (4.8 g, 56.8 mmol) in dichloromethane (100 mL) at room temperature, a solution of bromine (3.5 g, 21.7 mmol) in dichloromethane (30 mL) was added dropwise. The reaction mixture was stirred at room temperature for 30 minutes, filtered, and concentrated under vacuum. The residue was subjected to column chromatography on silica gel eluted with a hexanes and ethyl acetate gradient to provide the titled product.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated under vacuum
  3. washeluted with a hexanes and ethyl acetate gradient

Sources & evidence

ORD record
ord-b64154e75c174a42ab2a9e5d7eda0430
Source dataset
uspto-grants-2009_05
Patent number
US07538112B2

Reaction notes

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