Acetic Acid → HCID 178524929, compound

HRID 1053626Notes

Reaction equation

HRID 1053626 reaction equation
[Cl:1][C:2]1[CH:6]=[C:5]([C:7]([OH:9])=[O:8])[NH:4][N:3]=1.[B-](F)(F)(F)[F:11].[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1.C(O)(=O)C.[B-](F)(F)(F)F.[B-](F)(F)(F)F.C[N+]12CC[N+](F)(CC1)CC2>C(#N)C.CCOC(C)=O>[Cl:1][C:2]1[C:6]([F:11])=[C:5]([C:7]([OH:9])=[O:8])[NH:4][N:3]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 2724933SelectfluorHCID 152521271-Fluoro-4-methyl-1,4-diazabicyclo[2.2.2]octane-1,4-diium ditetrafluoroborateHCID 178524414HCID 178524414, compound

Product 1

HCID 178524929HCID 178524929, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-chloro-1H-pyrazole-5-carboxylic acid (200 mg, 1.37 mmol) was suspended in acetonitrile (3 mL) followed by the addition Selectfluor 11(550 mg, 1.55 mmol) and acetic acid (500 g, 8.33 mmol). The mixture was submitted to microwave irradiation, maintaining the temperature at 100 C for 2 h. An additional 550 mg of Selectfluor II was added and the reaction returned to the microwave where the temperature was maintained at 100 C for 1 h. The reaction mixture was diluted with 3 mL of EtOAc then washed with water (5 mL) three times. The solvent was stripped in vacuo and 3-chloro-4-fluoro-1H-pyrazole-5-carboxylic acid was isolated by semi prep HPLC (ACN/water+0.05% TFA).

Workup

  1. customirradiation
  2. temperaturemaintaining the temperature at 100 C for 2 h
  3. temperaturewas maintained at 100 C for 1 h
  4. washthen washed with water (5 mL) three times

Sources & evidence

ORD record
ord-7ce16699338b4a06925502a74c1b23ba
Source dataset
uspto-grants-2016_07
Patent number
US09394257B2

Reaction notes

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