Bromine → HCID 9889757, compound

HRID 2300192Notes

Reaction equation

HRID 2300192 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]([C:17]3[CH:22]=[CH:21][C:20]([S:23]([NH2:26])(=[O:25])=[O:24])=[CH:19][CH:18]=3)=[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][N:10]3[N:9]=2)=[CH:4][CH:3]=1.[Br:27]Br>C(Cl)(Cl)Cl>[Br:27][C:14]1[CH:13]=[CH:12][C:11]2[N:10]([N:9]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[C:16]=2[C:17]2[CH:22]=[CH:21][C:20]([S:23]([NH2:26])(=[O:25])=[O:24])=[CH:19][CH:18]=2)[CH:15]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 18376031HCID 18376031, compound

Product 1

HCID 9889757HCID 9889757, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A mixture of 4-[2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-3-yl]benzenesulfonamide (0.062 g 0.17 mmol) and bromine (0.03 g 0.17 mmol) in chloroform (3 ml) was heated under reflux for 24 hours. The reaction mixture was diluted with chloroform (20 ml), washed with M sodium thiosulphate (10 ml), water (10 ml) and dried. Removal of solvent gave a brown solid which was purified by SPE chromatography. Elution with cyclohexane/ethyl acetate (10/1) gave the title compound as a white solid (0.025 g 32%). MH+: 446, 448; NMR: (d6-acetone): δ 6.55 (2H, br) 7.05 (2H, t) 7.30 (1H, d) 7.45 (2H, d) 7.50 (2H, m) 7.55 (1H, d) 7.80 (2H, d) 8.80 (1H, s).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 24 hours
  3. washwashed with M sodium thiosulphate (10 ml), water (10 ml)
  4. customdried
  5. customRemoval of solvent
  6. customgave a brown solid which
  7. customwas purified by SPE chromatography
  8. washElution with cyclohexane/ethyl acetate (10/1)

Sources & evidence

ORD record
ord-3126151249da4c3095756e58afbeb7f3
Source dataset
uspto-grants-2002_12
Patent number
US06498166B1

Reaction notes

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