Water → HCID 67000707, compound

HRID 558630Notes

Reaction equation

HRID 558630 reaction equation
[CH:1]1([C:4]2[N:9]3[N:10]=[CH:11][C:12](C(O)=O)=[C:8]3[CH:7]=[C:6]([C:16]3[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=3)[CH:5]=2)[CH2:3][CH2:2]1.CC([O-])=O.[Na+].[I:31]Cl.O>C(O)(=O)C>[CH:1]1([C:4]2[N:9]3[N:10]=[CH:11][C:12]([I:31])=[C:8]3[CH:7]=[C:6]([C:16]3[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=3)[CH:5]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 24640Iodine chlorideHCID 517045Sodium AcetateHCID 67000775HCID 67000775, compound

Product 1

HCID 67000707HCID 67000707, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
23 °C

Procedure

A mixture of 7-cyclopropyl-5-(4-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyridine-3-carboxylic acid (example C.28 step 6) (1.03 g, 2.97 mmol) in acetic acid (40 mL) was refluxed for 20 h. Cooled to 23° C., added NaOAc (325 mg, 3.95 mmol) and ICl (2M in HOAc, 1.85 mL, 3.7 mmol) and the mixture was stirred at 23° C. for 2 h. Poured into water, filtered precipitate off, washed with water, dissolved in TBME, washed with sat. NaHCO3-sol.+little sat. Na2SO3-sol. and brine, dried over Na2SO4. Removal of the solvent in vacuum left the title compound as a light red solid (1.257 g, 99%). MS (ISP) 429.2 [(M+H)+].

Workup

  1. temperaturewas refluxed for 20 h
  2. filtrationfiltered precipitate off,
  3. washwashed with water
  4. dissolutiondissolved in TBME
  5. washwashed with sat. NaHCO3-sol
  6. dry with materialand brine, dried over Na2SO4
  7. customRemoval of the solvent in vacuum
  8. waitleft the title compound as a light red solid (1.257 g, 99%)

Sources & evidence

ORD record
ord-5d01b2509f144092af3297209bb87866
Source dataset
uspto-grants-2011_11
Patent number
US08063048B2

Reaction notes

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