Potassium Carbonate → HCID 86692534, compound

HRID 1748583Notes

Reaction equation

HRID 1748583 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]#[N:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[Br:26][C:27]1[CH:28]=[CH:29][C:30](F)=[N:31][CH:32]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([C:30]2[CH:29]=[CH:28][C:27]([Br:26])=[CH:32][N:31]=2)([C:14]#[N:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 1514443Tert-butyl 4-cyanopiperidine-1-carboxylateHCID 2724254Sodium bis(trimethylsilyl)amideHCID 27831685-Bromo-2-fluoropyridine

Product 1

HCID 86692534HCID 86692534, compoundYield 123.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of 4-cyanopiperidine-1-carboxylic acid tert-butyl ester (6.24 g) described in Reference Example 88 (1) in tetrahydrofuran (20 ml) was added a 1.9 M solution of sodium bis(trimethylsilyl)amide in tetrahydrofuran (21.2 ml) at 0° C., stirred for 45 minutes, then a solution of 5-bromo-2-fluoropyridine (2.76 g) in tetrahydrofuran (10 ml) was added thereto, and stirred at room temperature for 5 hours. To the reaction solution was added 10% potassium carbonate aqueous solution, extracted with ethyl acetate, washed with saturated brine, dried over anhydrous sodium sulfate, and then the solvent was evaporated in vacuo. The obtained residue was purified with silica gel chromatography (n-hexane/ethyl acetate) to give 4-(5-bromopyridin-2-yl)-4-cyanopiperidine-1-carboxylic acid tert-butyl ester (7.1 g) as a pale yellow oil.

Workup

  1. stirringstirred at room temperature for 5 hours
  2. extractionextracted with ethyl acetate
  3. washwashed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated in vacuo
  6. customThe obtained residue was purified with silica gel chromatography (n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-10551792903c41c490b9e3e95b0fcaa1
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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