N-bromobutanimide → Pyrazolo[1,5-a]pyridine, 3-bromo-6-chloro-2-(4-fluorophenyl)-

HRID 2300198Notes

Reaction equation

HRID 2300198 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([N:8]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[CH:10]=2)[CH:7]=1.C1C(=O)N([Br:25])C(=O)C1>CN(C=O)C>[Br:25][C:10]1[C:9]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)=[N:8][N:6]2[CH:7]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=12

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 183760346-Chloro-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridine

Product 1

HCID 18376027Pyrazolo[1,5-a]pyridine, 3-bromo-6-chloro-2-(4-fluorophenyl)-Yield 86.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-Chloro2-(4-fluorophenyl)pyrazolo[1,5-a]pyridine (2.48 g, 10.05 mmol) was dissolved in anhydrous DMF (160 ml) and treated with NBS (1.967 g) for 1 h. The reaction mixture was partitioned between ethyl acetate and water. The organic phase was separated, washed with water, dried and concentrated to give the title compound as a brown solid (2.827 g, 86%). (CDCl3) δ 7.19 (3H, t, J 9 Hz, H-3′+H-5); 7.48 (1H, d, J 9 Hz, H4); 8.05(2H, m, H-2′); 8.49 (1H, br s, H-7); Tlc SiO2 cyclohexane:ethyl acetate (3:1) Rf 0.74 detection uv254.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. customThe organic phase was separated
  3. washwashed with water
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-12c0b8e66c984800801d9d9b99eeb3a6
Source dataset
uspto-grants-2002_12
Patent number
US06498166B1

Reaction notes

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