Water → HCID 18376033, compound

HRID 2300188Notes

Reaction equation

HRID 2300188 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:18]=[C:11]3[CH:12]=[CH:13][C:14]([C:16]#[N:17])=[CH:15][N:10]3[N:9]=2)=[CH:4][CH:3]=1.C1C(=O)N([Br:26])C(=O)C1.O>CN(C=O)C>[Br:26][C:18]1[C:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)=[N:9][N:10]2[CH:15]=[C:14]([C:16]#[N:17])[CH:13]=[CH:12][C:11]=12

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 18376035HCID 18376035, compound

Product 1

HCID 18376033HCID 18376033, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-(4-fluorophenyl)pyrazolo[1,5-a]pyridine-6-carbonitrile (0.6 g 2.53 mmol) and NBS (0.5 g 2.8 mmol) in DMF (10 ml) was stirred at room temperature for 2 hr. The reaction was poured into water (100 ml) and extracted with ethyl acetate (2×30 ml). The combined extracts were washed with water (30 ml), brine (30 ml), dried and purified by biotage chromatography. Elution with cyclohexane/ethyl acetate (20:1) gave the title compound as a white solid (0.483 g 61%). NMR: (CDCl3): δ 7.21 (2H, t) 7.30 (1H, dd) 7.62 (1H, dd) 8.06 (2H, m) 8.80 (1H, s).

Workup

  1. extractionextracted with ethyl acetate (2×30 ml)
  2. washThe combined extracts were washed with water (30 ml), brine (30 ml)
  3. customdried
  4. custompurified by biotage chromatography
  5. washElution with cyclohexane/ethyl acetate (20:1)

Sources & evidence

ORD record
ord-4dd65a6baea143678ad908279d57415d
Source dataset
uspto-grants-2002_12
Patent number
US06498166B1

Reaction notes

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