Potassium Carbonate → HCID 59843243, compound

HRID 2196540Notes

Reaction equation

HRID 2196540 reaction equation
Br[C@H:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3]1.C(=O)([O-])[O-].[K+].[K+].[O:20]1[CH:24]=[CH:23][CH:22]=[C:21]1[C:25]1[NH:29][N:28]=[C:27]([C:30]([F:33])([F:32])[F:31])[CH:26]=1.O1C=CC=C1C1N(C2C=C(C#N)SC=2)N=C(C(F)(F)F)C=1.O.NN>CN(C=O)C>[O:20]1[CH:24]=[CH:23][CH:22]=[C:21]1[C:25]1[N:29]([C@@H:2]2[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3]2)[N:28]=[C:27]([C:30]([F:33])([F:31])[F:32])[CH:26]=1

Participants

7

Reactant 5

HCID 11430Potassium CarbonateHCID 24654Hydrazine hydrate (1:1)HCID 34179480tert-Butyl (3S)-3-bromopyrrolidine-1-carboxylateHCID 598432044-(5-(furan-2-yl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)thiophene-2-carbonitrileHCID 178506075HCID 178506075, compound

Product 1

HCID 59843243HCID 59843243, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of 72 (681 mg, 2.72 mmol) in DMF (9.894 mL) was added potassium carbonate (855 mg, 6.18 mmol), and then 5-(furan-2-yl)-3-(trifluoromethyl)-1H-pyrazole (500 mg, 2.474 mmol) [made by following the procedure described above for the synthesis of compound 14 (scheme 2, example 1c, step 4), except using hydrazine hydrate instead of 13 as the starting material]. The resulting solution was allowed to stir at 100° C. for 1 h. The mixture was quenched with water and extracted with ethyl acetate, washed with brine, dried (MgSO4) filtered and concentrated. The residue was purified by silica gel column chromatography with gradient of EtOAc (10-20%) in hexanes to afford 73 (340 mg, 37%) as a colorless oil. LRMS (ESI): calc. 371.1; found 394.0 (MNa)+.

Workup

  1. customThe mixture was quenched with water
  2. extractionextracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography with gradient of EtOAc (10-20%) in hexanes

Sources & evidence

ORD record
ord-342666d769de4839a007dbf02e282d1a
Source dataset
uspto-grants-2012_12
Patent number
US08338437B2

Reaction notes

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