Bromine → HCID 69173116, compound

HRID 2114835Notes

Reaction equation

HRID 2114835 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([C:20]([NH:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([F:30])=[C:26]([Cl:31])[CH:25]=2)=[O:21])=[CH:11][N:12]2[CH2:17][CH2:16][N:15]([CH3:18])[C:14](=[O:19])[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:20]([NH:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([F:30])=[C:26]([Cl:31])[CH:25]=2)=[O:21])=[C:11]([Br:37])[N:12]2[CH2:17][CH2:16][N:15]([CH3:18])[C:14](=[O:19])[C:13]=12)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 516892Sodium BicarbonateHCID 69173221HCID 69173221, compound

Product 1

HCID 69173116HCID 69173116, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 8-(benzyloxy)-N-(3-chloro-4-fluorobenzyl)-2-methyl-1-oxo-1,2,3,4-tetrahydropyrrolo-[1,2-a]pyrazine-7-carboxamide (0.23 g, 0.51 mmol) and sodium bicarbonate (0.52 g, 6.13 mmol) in dichloromethane (50 mL) at 0° C., a solution of bromine in dichloromethane (0.5 M, 1.1 mL, 0.55 mmol) was added. The reaction mixture was stirred at room temperature for 2 h, filtered, and concentrated under vacuum. The residue was subjected to column chromatography on silica gel eluted with ethyl acetate. Collection and concentration of appropriate fractions provided the titled product.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated under vacuum
  3. washeluted with ethyl acetate
  4. customCollection and concentration of appropriate fractions

Sources & evidence

ORD record
ord-f6a6cf9acc8d49658dfec525bcc3ae76
Source dataset
uspto-grants-2008_10
Patent number
US07435735B2

Reaction notes

Loading…