N-bromobutanimide → HCID 86690318, compound

HRID 1428667Notes

Reaction equation

HRID 1428667 reaction equation
[CH2:1]([O:3][C:4](=[O:34])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]1[C:15]2=[N:16][C:17]([C:27]3[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=3)=[C:18]([C:20]3[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=3)[N:19]=[C:14]2[CH:13]=[CH:12]1)[CH3:2].[Br:35]N1C(=O)CCC1=O>C(Cl)Cl>[Br:35][C:13]1[C:14]2[C:15](=[N:16][C:17]([C:27]3[CH:28]=[CH:29][C:30]([CH3:33])=[CH:31][CH:32]=3)=[C:18]([C:20]3[CH:21]=[CH:22][C:23]([CH3:26])=[CH:24][CH:25]=3)[N:19]=2)[N:11]([CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:34])[CH:12]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 71657498HCID 71657498, compound2×

Product 1

HCID 86690318HCID 86690318, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

7-(2,3-Di-p-tolyl-pyrrolo[2,3-b]pyrazin-5-yl)-heptanoic acid ethyl ester (Intermediate B) (135 mg, 0.296 mmol) in DCM (5 ml) was treated with N-bromosuccinimide (52.7 mg, 0.296 mmol) and the reaction mixture was stirred at room temperature for 16 hours. The mixture was diluted with DCM (50 ml) and washed with water (×2), brine (×1) and the organic solvent was removed under reduced pressure. Purification of the crude product by chromatography on silica using a gradient from 0-10% EtOAc in iso-hexane afforded the titled compound as an orange oil;

Workup

  1. washwashed with water (×2), brine (×1)
  2. customthe organic solvent was removed under reduced pressure
  3. customPurification of the crude product by chromatography on silica using a gradient from 0-10% EtOAc in iso-hexane

Sources & evidence

ORD record
ord-d05a81516da34d3f934c916f41755853
Source dataset
uspto-grants-2015_01
Patent number
US08937069B2

Reaction notes

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