Water → HCID 59843183, compound

HRID 2196543Notes

Reaction equation

HRID 2196543 reaction equation
I[CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[F:15][C:16]([F:28])([F:27])[C:17]1[CH:21]=[C:20]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[NH:19][N:18]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH2:25]([O:24][C:22]([C:20]1[N:19]([CH:2]2[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]2)[N:18]=[C:17]([C:16]([F:27])([F:28])[F:15])[CH:21]=1)=[O:23])[CH3:26]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 10892302Tert-butyl 4-iodopiperidine-1-carboxylateHCID 178468958HCID 178468958, compound

Product 1

HCID 59843183HCID 59843183, compoundYield 39.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

tert-Butyl 4-iodopiperidine-1-carboxylate (5.683, 18.26 mmol, E.G. Corley et al, JOC, 2004, 69, 5120-5123) in DMF (30.7 ml) was added to a mixture of ethyl 3-(trifluoromethyl)-1H-pyrazole-5-carboxylate (3.2 g, 15.37 mmol, M.-A. Plancquaert et al, Tetrahedron, 52, 4383-4396) and potassium carbonate 95.31 g, 38.4 mmol) and the mixture was stirred at 80° C. for 16 h. After cooling, water was added and the mixture was extracted with EtOAc, and the organic extraxts were dried, filtered and concentrated. Chromatographic purification of the residue by Biotage (5-20% EtOAc in Hexanes, 25M column) gave compound 93 as colorless oil (2.4 g, 39.9% yield). LRMS (ESI): calc. 391.4; found 414.1 (M+Na)+.

Workup

  1. temperatureAfter cooling
  2. extractionthe mixture was extracted with EtOAc
  3. customthe organic extraxts were dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customChromatographic purification of the residue by Biotage (5-20% EtOAc in Hexanes, 25M column)

Sources & evidence

ORD record
ord-93a7ca9a478d4fe792260820b42615ad
Source dataset
uspto-grants-2012_12
Patent number
US08338437B2

Reaction notes

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