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

HRID 341236Notes

Reaction equation

HRID 341236 reaction equation
[I:1]N1C(=O)CCC1=O.[F:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[N: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[N: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-Iodosuccinimide2×HCID 593211056-(4-Fluoro-phenyl)-pyrazolo[1,5-a]pyrazine

Product 1

HCID 593209786-(4-Fluoro-phenyl)-3-iodo-pyrazolo[1,5-a]pyrazineYield 76.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
50 °C

Procedure

N-iodosuccinimide (13 mg, 0.06 mmol) was added in one portion to a stirred solution of 6-(4-fluoro-phenyl)-pyrazolo[1,5-a]pyrazine (11 mg, 0.05 mmol) in dry DMF (0.5 ml) at RT under N2. After 30 minutes, a further portion of N-iodosuccinimide (13 mg, 0.06 mmol) in DMF (0.2 mmol) was added. After a further 30 minutes at RT the mixture was heated to 50° C. for 90 minutes. After cooling to RT, the reaction was quenched with saturated aqueous sodium thiosulphate/saturated NaHCO3 (1:1, 1 ml). The mixture was stirred at RT for 1 hour then partitioned between CH2Cl2/H2O. The mixture was passed through a phase separating cartridge. The organic layer was evaporated to give the title compound (13 mg, solid). 1H NMR (400 MHz, CDCl3): 9.01 (1H, d), 8.69 (1H, d), 8.05 (1H, s), 8.00-7.90 (2H, m), 7.24-7.14 (2H, m).

Workup

  1. temperatureAfter cooling to RT
  2. customthe reaction was quenched with saturated aqueous sodium thiosulphate/saturated NaHCO3 (1:1, 1 ml)
  3. customthen partitioned between CH2Cl2/H2O
  4. customseparating cartridge
  5. customThe organic layer was evaporated

Sources & evidence

ORD record
ord-b8bd3874d919435cafd8403dfcd14ec5
Source dataset
uspto-grants-2014_11
Patent number
US08895745B2

Reaction notes

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