N-bromobutanimide → 3-Bromo-8-cyano-7-(4-phenylpiperidinyl)[1,2,4]triazolo[4,3-a]pyridine

HRID 587650Notes

Reaction equation

HRID 587650 reaction equation
[C:1]([C:3]1[C:4]2[N:5]([CH:21]=[N:22][N:23]=2)[CH:6]=[CH:7][C:8]=1[N:9]1[CH2:14][CH2:13][CH:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:11][CH2:10]1)#[N:2].[Br:24]N1C(=O)CCC1=O>C(Cl)Cl>[Br:24][C:21]1[N:5]2[CH:6]=[CH:7][C:8]([N:9]3[CH2:14][CH2:13][CH:12]([C:15]4[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=4)[CH2:11][CH2:10]3)=[C:3]([C:1]#[N:2])[C:4]2=[N:23][N:22]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 667888318-Cyano-7-(4-phenylpiperidinyl)[1,2,4]triazolo[4,3-a]pyridine

Product 1

HCID 574596343-Bromo-8-cyano-7-(4-phenylpiperidinyl)[1,2,4]triazolo[4,3-a]pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of intermediate D8 (0.49 g, 1.615 mmol) in DCM (20 ml) was added N-bromosuccinimide (0.316 g, 1.777 mmol). The resulting mixture was stirred at r.t. for 1.5 h. The mixture was carefully washed with NaHCO3 (aqueous sat. solution) and extracted with DCM. The organic layer was separated, dried (Na2SO4) and concentrated in vacuo to yield intermediate D97 (0.48 g, 78%).

Workup

  1. washThe mixture was carefully washed with NaHCO3 (aqueous sat. solution)
  2. extractionextracted with DCM
  3. customThe organic layer was separated
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customto yield intermediate D97 (0.48 g, 78%)

Sources & evidence

ORD record
ord-580bc0fdf34e42e78eb6bf836429f059
Source dataset
uspto-grants-2016_01
Patent number
US09226930B2

Reaction notes

Loading…