N-bromobutanimide → (2-Amino-5-bromopyridin-3-yl)(6-bromopyridin-2-yl)methanone

HRID 401470Notes

Reaction equation

HRID 401470 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Br:16])[N:11]=2)=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[Br:17]N1C(=O)CCC1=O>C(#N)C>[NH2:1][C:2]1[C:7]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Br:16])[N:11]=2)=[O:9])=[CH:6][C:5]([Br:17])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 57690673HCID 57690673, compound

Product 1

HCID 57690616(2-Amino-5-bromopyridin-3-yl)(6-bromopyridin-2-yl)methanoneYield 57.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of (2-aminopyridin-3-yl)(6-bromopyridin-2-yl)methanone (5.76 g, 20.7 mmol) in acetonitrile (120 ml) was added N-bromosuccinimide (4.05 g, 22.77 mmol). The resulting mixture was stirred at room temperature for 1 hour before mixture was concentrated in vacuo to approximately 20 ml. The solid was then collected by filtration and washed with minimal acetonitrile and dried to leave title compound as a brown solid (4.23 g, 57%). 1H NMR (DMSO-d6) 7.93-7.89 (4H, m), 8.03-7.99 (1H, m), 8.22 (1H, d), 8.36 (1H, d). ES+ 357.99.

Workup

  1. concentrationwas concentrated in vacuo to approximately 20 ml
  2. filtrationThe solid was then collected by filtration
  3. washwashed with minimal acetonitrile
  4. customdried

Sources & evidence

ORD record
ord-d037a62513874dbb9293e3f8ec62d348
Source dataset
uspto-grants-2014_06
Patent number
US08741931B2

Reaction notes

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