N-Iodosuccinimide → 6-(4-Fluoro-phenyl)-3-iodo-pyrazolo[1,5-a]pyridine

HRID 341238Notes

Reaction equation

HRID 341238 reaction equation
[I:1]N1C(=O)CCC1=O.[F:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:17]=[CH:18][C:19]3[N:20]([N:22]=[CH:23][CH:24]=3)[CH:21]=2)=[CH:12][CH:11]=1>CN(C=O)C>[F:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]2[CH:17]=[CH:18][C:19]3[N:20]([N:22]=[CH:23][C:24]=3[I:1])[CH:21]=2)=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 59277825HCID 59277825, compound

Product 1

HCID 592778056-(4-Fluoro-phenyl)-3-iodo-pyrazolo[1,5-a]pyridineYield 78.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-iodosuccinimide (630 mg, 2.8 mmol) was added in one portion to a stirred solution of 6-(4-fluoro-phenyl)-pyrazolo[1,5-a]pyridine (500 mg, 2.4 mmol) in dry DMF (6 ml) at RT under N2. After 45 minutes, the reaction was quenched with saturated aqueous sodium thiosulphate/saturated NaHCO3 (1:1, 40 ml). The mixture was stirred at RT for 15 minutes then partitioned between EtOAc/H2O. The organic layer was washed with water (×1), brine (×1), then dried (MgSO4), filtered and evaporated. The residue was purified trituration with petrol to give the title compound (635 mg, solid). 1H NMR (400 MHz, CDCl3): 8.61 (1H, s), 7.98 (1H, s), 7.57-7.51 (3H, m), 7.42 (1H, dd), 7.22-7.13 (2H, m).

Workup

  1. customthe reaction was quenched with saturated aqueous sodium thiosulphate/saturated NaHCO3 (1:1, 40 ml)
  2. customthen partitioned between EtOAc/H2O
  3. washThe organic layer was washed with water (×1), brine (×1)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified trituration with petrol

Sources & evidence

ORD record
ord-91c276ba99b246d19a81854d267ef76d
Source dataset
uspto-grants-2014_11
Patent number
US08895745B2

Reaction notes

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