Potassium Carbonate → HCID 89852354, compound

HRID 1746903Notes

Reaction equation

HRID 1746903 reaction equation
Cl[CH2:2][C:3]1[CH:7]=[CH:6][N:5]([C:8]2[N:18]=[CH:17][CH:16]=[CH:15][C:9]=2[C:10]([O:12][CH2:13][CH3:14])=[O:11])[N:4]=1.[F:19][C:20]1([F:26])[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[F:19][C:20]1([F:26])[CH2:25][CH2:24][N:23]([CH2:2][C:3]2[CH:7]=[CH:6][N:5]([C:8]3[N:18]=[CH:17][CH:16]=[CH:15][C:9]=3[C:10]([O:12][CH2:13][CH3:14])=[O:11])[N:4]=2)[CH2:22][CH2:21]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27583524,4-DifluoropiperidineHCID 89851983HCID 89851983, compound

Product 1

HCID 89852354HCID 89852354, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The mixture of ethyl 2-(3-(chloromethyl)-1H-pyrazol-1-yl)nicotinate (500 mg, 1.882 mmol), 4,4-difluoropiperidine (328 mg, 2.7 mmol), and K2CO3 were stirred at room temperature in acetonitrile (25 mL) until completion of the reaction. The mixture was concentrated, pardoned between water and dichlormethane (60 mL), the organic layer separated, washed twice with water, dried (MgSO4), filtered and dried to give a brown oil, which then was purified by chromatography over silica gel (CH2Cl2+methanol) to yield 620 mg of the title compound as clear oil. ESI-MS [M+H]+: 351.15.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe organic layer separated
  3. washwashed twice with water
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customdried
  7. customto give a brown oil, which
  8. customthen was purified by chromatography over silica gel (CH2Cl2+methanol)

Sources & evidence

ORD record
ord-b9396a00e43c45d0988ba3723011b8c7
Source dataset
uspto-grants-2015_10
Patent number
US09150545B2

Reaction notes

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