Lawesson's reagent → HCID 59632628, compound

HRID 2369104Notes

Reaction equation

HRID 2369104 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:9]=[C:8]([C:10]2[S:11][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([S:21]([CH3:24])(=[O:23])=[O:22])[CH:16]=3)=[CH:13][CH:14]=2)[N:7]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[C:31]([F:34])([F:33])[F:32])[N:6]=1)=O.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:44])=CC=1>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]([C:5]1[CH:9]=[C:8]([C:10]2[S:11][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([S:21]([CH3:24])(=[O:22])=[O:23])[CH:16]=3)=[CH:13][CH:14]=2)[N:7]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[C:31]([F:33])([F:34])[F:32])[N:6]=1)=[S:44]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 59633227HCID 59633227, compound

Product 1

HCID 59632628HCID 59632628, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a 50 mL round bottom flask attached with condenser was added 5-[5-(3-Methanesulfonyl-phenyl)-thiophen-2-yl]-1-(2-trifluoromethyl-phenyl)-1H-pyrazole-3-carboxylic acid methyl ester (326 mg, 644 μmmol), Lawesson's reagent (520 mg, 129 mmol) and anhydrous toluene (23 mL). The reaction solution was stirred at reflux for 1 day. The reaction solution was concentrated in vacuo, and the crude material was chromatographed through a 25 g SiO2 column using a gradient of 100% Hx to 50% EtOAc to afford 302 mg (90% yield) of the title compound. MS (ES) 523.3 [M+H]+, 545.0 (M+Na)+.

Workup

  1. customTo a 50 mL round bottom flask attached with condenser
  2. temperatureat reflux for 1 day
  3. concentrationThe reaction solution was concentrated in vacuo
  4. customthe crude material was chromatographed through a 25 g SiO2 column

Sources & evidence

ORD record
ord-c2d23c2ac7634f0486eb74919b249a44
Source dataset
uspto-grants-2014_04
Patent number
US08703805B2

Reaction notes

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