Formic Acid → HCID 59632117, compound

HRID 2369069Notes

Reaction equation

HRID 2369069 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([C:13]2[S:17][C:16]([C:18]3[CH:19]=[C:20]([CH:32]=[CH:33][CH:34]=3)[O:21][C:22]([CH3:31])([CH3:30])[C:23]([O:25]C(C)(C)C)=[O:24])=[CH:15][CH:14]=2)=[CH:11][C:10]([C:35]([F:38])([F:37])[F:36])=[N:9]1.C(O)=O>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([C:13]2[S:17][C:16]([C:18]3[CH:19]=[C:20]([CH:32]=[CH:33][CH:34]=3)[O:21][C:22]([CH3:31])([CH3:30])[C:23]([OH:25])=[O:24])=[CH:15][CH:14]=2)=[CH:11][C:10]([C:35]([F:38])([F:36])[F:37])=[N:9]1

Participants

4

Reactant 2

HCID 284Formic AcidHCID 59631951HCID 59631951, compound

Product 1

HCID 59632117HCID 59632117, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 2-(3-(5-(1-(2-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)thiophen-2-yl)phenoxy)-2-methylpropanoate (47 mg, 84 μmol) in dichloromethane (0.5 mL) was added formic acid (1.0 mL). The resulting pale orange solution was allowed to stir at ambient temperature. After 5 hours at ambient temperature, LC/MS analysis of the reaction showed ˜5% of the starting ester remaining. After 7 hours stirring at ambient temperature the reaction mixture was concentrated under reduced pressure to afford crude product. This material was purified by flash column chromatography eluting with a gradient from CH2Cl2 to 10% MeOH/CH2Cl2 to afford 2-(3-(5-(1-(2-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)thiophen-2-yl)phenoxy)-2-methylpropanoic acid (21.7 mg, 51% yield) as an off white foam. MS(ES): 509 [M+H]+.

Workup

  1. stirringAfter 7 hours stirring at ambient temperature the reaction mixture
  2. concentrationwas concentrated under reduced pressure
  3. customto afford crude product
  4. customThis material was purified by flash column chromatography
  5. washeluting with a gradient from CH2Cl2 to 10% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-3bfd1395956d41e197a5ed38864c969f
Source dataset
uspto-grants-2014_04
Patent number
US08703805B2

Reaction notes

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