Potassium Carbonate → HCID 67111103, compound

HRID 540784Notes

Reaction equation

HRID 540784 reaction equation
[CH2:1]([N:3]1[C:7]([C:8]2[CH:9]=[C:10]3[C:14](=[CH:15][CH:16]=2)[CH2:13][CH:12]([NH:17]C(=O)OC(C)(C)C)[CH2:11]3)=[CH:6][C:5](=[O:25])[NH:4]1)[CH3:2].F[C:27]1[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=1.C([O-])([O-])=O.[K+].[K+]>CS(C)=O.C(Cl)Cl>[CH2:1]([N:3]1[C:7]([C:8]2[CH:9]=[C:10]3[C:14](=[CH:15][CH:16]=2)[CH2:13][CH:12]([NH2:17])[CH2:11]3)=[CH:6][C:5]([O:25][C:27]2[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=2)=[N:4]1)[CH3:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 67873Benzene, 1-fluoro-4-(trifluoromethyl)-HCID 69932691HCID 69932691, compound

Product 1

HCID 67111103HCID 67111103, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of tert-butyl [5-(2-ethyl-5-oxo-2,5-dihydro-1H-pyrazol-3-yl)-2,3-dihydro-1H-inden-2-yl]carbamate (28 mg, 0.082 mmol) in DMSO (1 mL) was treated with fluoro-4-(trifluoromethyl)benzene (100 mg, 0.609 mmol) and K2CO3 (20 mg, 0.15 mmol). The suspension was stirred for 40 min at 140° C. until no SM remained. Significant Boc thermolysis was observed under these conditions. The reaction was cooled, diluted with DCM, extracted with 1 N NaOH, water, dried (Na2SO4), concentrated. The residue was dissolved in 0.9 mL of DCM and 0.1 mL of TFA, then stirred for 1 hour, diluted with DCM, extracted with 1 N NaOH, water, dried (Na2SO4), and finally concentrated to give 5-{1-ethyl-3-[4-(trifluoromethyl)phenoxy]-1H-pyrazol-5-yl}-2,3-dihydro-1H-inden-2-amine (18 mg, 57%): MS cal'd for C21H21F3N3O [M+H]+388.2. found 388.1.

Workup

  1. temperatureThe reaction was cooled
  2. extractionextracted with 1 N NaOH, water
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in 0.9 mL of DCM
  6. stirring0.1 mL of TFA, then stirred for 1 hour
  7. additiondiluted with DCM
  8. extractionextracted with 1 N NaOH, water
  9. dry with materialdried (Na2SO4)
  10. concentrationfinally concentrated

Sources & evidence

ORD record
ord-87304b8c4ac24230acc604fff11acd44
Source dataset
uspto-grants-2014_10
Patent number
US08871796B2

Reaction notes

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