N-bromobutanimide → HCID 58381981, compound

HRID 1628030Notes

Reaction equation

HRID 1628030 reaction equation
[N:1]1[C:6]([CH2:7][NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:5][N:4]=[C:3]2[NH:16][CH:17]=[CH:18][C:2]=12.C1C(=O)N([Br:26])C(=O)C1>CN(C=O)C>[Br:26][C:18]1[C:2]2[C:3](=[N:4][CH:5]=[C:6]([CH2:7][NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[N:1]=2)[NH:16][CH:17]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 58382111HCID 58382111, compound

Product 1

HCID 58381981HCID 58381981, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

tert-Butyl (5H-pyrrolo[2,3-b]pyrazin-2-yl)methylcarbamate (2.45 g, 9.87 mmol) in DMF (50 mL) was treated with NBS (1.76 g, 9.87 mmol) at P. After about 15 min the solvents were removed under reduced pressure then the material was suspended in water (25 mL). The slurry was stirred for about 30 min then the solids were collected by filtration and dried to a constant weight under vacuum at about 70° C. to give tert-butyl (7-bromo-5H-pyrrolo[2,3-b]pyrazin-2-yl)methylcarbamate (3.15 g, 98%): LC/MS (Table 2, Method b) Rt=1.99 min; MS m/z 327 (M+H)+.

Workup

  1. customAfter about 15 min the solvents were removed under reduced pressure
  2. filtrationthe solids were collected by filtration
  3. customdried to a constant weight under vacuum at about 70° C.

Sources & evidence

ORD record
ord-d25b44d19fea47109ae023d71ea67142
Source dataset
uspto-grants-2014_07
Patent number
US08785639B2

Reaction notes

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