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Ethanol → 7-Trifluoromethyl-5-(4-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyridine-3-carboxylic acid ethyl ester

HRID 1293710
Notes
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Reaction equation

HRID 1293710 reaction equation
[NH2:1][N:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)=[CH:4][C:3]1=S.ClC1S[C:26](S(Cl)(=O)=O)=[C:27]([CH3:29])N=1.C([O-])(O)=[O:35].[Na+].[CH3:39][CH2:40][OH:41]>>[CH2:40]([O:41][C:29]([C:27]1[CH:26]=[N:1][N:2]2[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5]([C:12]3[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=3)=[CH:4][C:3]=12)=[O:35])[CH3:39]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 4

HCID 702EthanolHCID 516892Sodium BicarbonateHCID 120942502-Chloro-4-methyl-1,3-thiazole-5-sulfonyl chloride4×HCID 866080141-amino-6-trifluoromethyl-4-(4-trifluoromethyl-phenyl)-1H-pyridine-2-thione

Product 1

HCID 866080137-Trifluoromethyl-5-(4-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyridine-3-carboxylic acid ethyl ester
Yield 62%

Procedure

A solution of 1-amino-6-trifluoromethyl-4-(4-trifluoromethyl-phenyl)-1H-pyridine-2-thione (example C.22 step 6) (3.14 g, 9.28 mmol) and 2-chloro-3-oxo-propionic acid ethyl ester (example C.22 reagent 1) (4.19 g, 27.85 mmol) in EtOH (45 mL) was refluxed for 20 h, the added again 2-chloro-3-oxo-propionic acid ethyl ester (example C.22 reagent 1) (2.20 g, 14.61 mmol) and refluxing was continued for another 18 h. Poured into sat. NaHCO3-sol., extracted with EtOAc, washed the organic layer with brine, dried over Na2SO4 and evaporated to leave a residue, which was purified by flash chromatography (600 g SiO2) with heptane/EtOAc 9:1, followed by trituration with heptane (ca. 50 mL) at −70° C. to give the title compound as a light yellow solid (2.30 g, 62%). MS (ISP) 403 [(M+H)+]; mp 130° C.

Workup

  1. customwas refluxed for 20 h
  2. temperaturerefluxing
  3. extraction, extracted with EtOAc
  4. washwashed the organic layer with brine
  5. dry with materialdried over Na2SO4
  6. customevaporated
  7. customto leave a residue, which
  8. customwas purified by flash chromatography (600 g SiO2) with heptane/EtOAc 9:1
  9. customfollowed by trituration with heptane (ca. 50 mL) at −70° C.

Sources & evidence

ORD record
ord-195c3dcd8525489180f2af90dd75e79a
Source dataset
uspto-grants-2007_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07238808B2

Reaction notes

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