Water → 2-(4-Fluorophenyl)-3-bromopyrazolo[1,5-a]pyridine

HRID 1374696Notes

Reaction equation

HRID 1374696 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16](C(O)=O)=[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][N:10]3[N:9]=2)=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+].[Br:25]N1C(=O)CCC1=O.O>CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]([Br:25])=[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][N:10]3[N:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 219486812-(4-Fluorophenyl)pyrazolo[1,5-A]pyridine-3-carboxylic acid

Product 1

HCID 219486782-(4-Fluorophenyl)-3-bromopyrazolo[1,5-a]pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(4-fluorophenyl)-pyrazolo[1,5-a]pyridine-3-carboxylic acid (0.96 g, 3.75 mmol) in dry DMF (10 mL) was added sodium bicarbonate (0.95 g, 11.3 mmol) followed by N-bromosuccinimide (0.667 g, 3.75 mmol) and the mixture was stirred at room temperature under a nitrogen atmosphere for about 90 min. The mixture was poured into water (300 mL) and the resulting solid was collected by filtration and washed with water. The solid was dissolved in 10:1 chloroform:methanol (10 mL) and filtered through a pad (0.5 cm) of silica gel using 10:1 chloroform:methanol as eluent. The filtrate was evaporated to leave the title compound as a tan solid, 0.87 g (80%). 1H NMR (d6-DMSO) δ 8.7 (d, 1H, J=6.9 Hz), 8.02 (dd, 2H, J=8.7, 5.7 Hz), 7.61 (d, 1H, J=8.4 Hz), 7.40 (t, 1H, J=6 Hz), 7.38 (t, 2H, J=9 Hz), 7.04 (t, 1H, J=6.9 Hz). MS (+ve ion electrospray) 293 (100), (MH+).

Workup

  1. filtrationthe resulting solid was collected by filtration
  2. washwashed with water
  3. dissolutionThe solid was dissolved in 10:1 chloroform
  4. filtrationmethanol (10 mL) and filtered through a pad (0.5 cm) of silica gel using 10:1 chloroform
  5. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-285e683ca57e4b3b9a5171555b04cfac
Source dataset
uspto-grants-2007_01
Patent number
US07166597B2

Reaction notes

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