Sodium Carbonate Decahydrate → [2-(4-Ethoxycarbonyl-4-fluoropiperidin-1-yl)pyrimidin-5-yl]boronic acid

HRID 626957Notes

Reaction equation

HRID 626957 reaction equation
Cl.[F:2][C:3]1([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.Cl[C:15]1[N:20]=[CH:19][C:18]([B:21]([OH:23])[OH:22])=[CH:17][N:16]=1.O.O.O.O.O.O.O.O.O.O.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[CH2:12]([O:11][C:9]([C:3]1([F:2])[CH2:4][CH2:5][N:6]([C:15]2[N:20]=[CH:19][C:18]([B:21]([OH:23])[OH:22])=[CH:17][N:16]=2)[CH2:7][CH2:8]1)=[O:10])[CH3:13]

Participants

5

Reactant 3

HCID 151402Sodium Carbonate DecahydrateHCID 21747362(2-Chloropyrimidin-5-yl)boronic acidHCID 24729616Ethyl 4-Fluoropiperidine-4-carboxylate Hydrochloride

Product 1

HCID 89924179[2-(4-Ethoxycarbonyl-4-fluoropiperidin-1-yl)pyrimidin-5-yl]boronic acidYield 97%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of ethyl 4-fluoropiperidine-4-carboxylate hydrochloride (2 g, 9.4491 mmol), (2-chloropyrimidin-5-yl)boronic acid (1.5426 g, 9.4493 mmol) and sodium carbonate decahydrate (2.53 g, 23.6 mmol) in ethanol (15 mL) was stirred at 60° C. for 12 h. The reaction mixture was filtered through celite, the solvent was evaporated and the residue was dried under vacuum to give the title compound (2.7 g, 97%) as a pale yellow gum, which was used without further purification. LCMS (pH 10) MH+ 298, RT 1.19 minutes.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. customthe solvent was evaporated
  3. customthe residue was dried under vacuum

Sources & evidence

ORD record
ord-0c0272d93b3e43b2a75d7470f8a95d60
Source dataset
uspto-grants-2016_04
Patent number
US09309243B2

Reaction notes

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