Toluene → 4-(5-(furan-2-yl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)thiophene-2-carbonitrile

HRID 2196501Notes

Reaction equation

HRID 2196501 reaction equation
Cl.[NH:2]([C:4]1[CH:5]=[C:6]([C:9]#[N:10])[S:7][CH:8]=1)[NH2:3].[F:11][C:12]([F:24])([F:23])[C:13](=O)[CH2:14][C:15]([C:17]1[O:18][CH:19]=[CH:20][CH:21]=1)=O.C1(C)C=CC=CC=1>CC(O)=O>[O:18]1[CH:19]=[CH:20][CH:21]=[C:17]1[C:15]1[N:2]([C:4]2[CH:5]=[C:6]([C:9]#[N:10])[S:7][CH:8]=2)[N:3]=[C:13]([C:12]([F:11])([F:23])[F:24])[CH:14]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 675944,4,4-Trifluoro-1-(2-furanyl)-1,3-butanedioneHCID 69299496HCID 69299496, compound

Product 1

HCID 598432044-(5-(furan-2-yl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)thiophene-2-carbonitrileYield 74%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of compound 13 (0.701 g, 3.99 mmol) in AcOH (10 mL) was added 4,4,4-trifluoro-1-(2-furyl)-1,3-butanedione (0.591 mL, 3.99 mmol). The solution was stirred at 80 degrees for a total of 22 minutes. After the addition of toluene to the brown solution it was concentrated under reduced pressure to a brown-green sludge. The sludge was dry loaded onto a 40M Biotage column and then eluted with a gradient of 5 to 20% ethyl acetate in hexanes to furnish compound 14 (0.909 g, 74%) as a light brown oil which solidified upon standing. LRMS (ESI): calc. 309.2; found 310.1 (MH)+.

Workup

  1. concentrationwas concentrated under reduced pressure to a brown-green sludge
  2. customThe sludge was dry
  3. washeluted with a gradient of 5 to 20% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-1b9d8e0e52f84644aa4b820ffc429ae1
Source dataset
uspto-grants-2012_12
Patent number
US08338437B2

Reaction notes

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