2-Fluoro-6-methylpyridine → HCID 57430044, compound

HRID 1169827Notes

Reaction equation

HRID 1169827 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[N:3]=1.[C:9]([CH:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]1)#[N:10].C[Si]([N-][Si](C)(C)C)(C)C.[K+]>C1(C)C=CC=CC=1.[Cl-].[Na+].O>[C:9]([C:11]1([C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[N:3]=2)[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]1)#[N:10]

Participants

6

Reactant 3

HCID 960902-Fluoro-6-methylpyridineHCID 1514443Tert-butyl 4-cyanopiperidine-1-carboxylateHCID 3251421Potassium bis(trimethylsilyl)amide

Product 1

HCID 57430044HCID 57430044, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 2-fluoro-6-methylpyridine (6.67 g, 60 mmole) in toluene (40 mL) was added tert-butyl 4-cyanopiperidine-1-carboxylate (I-1) (4.22 g, 20 mmole) and 0.5M solution of KHMDS (48 mL, 24 mmole). The reaction mixture was stirred 2h min at rt ° C. After this time, LCMS indicated that the reaction was completion. The reaction mixture was poured into brine (150 mL) and extracted with EtOAc (3×150 mL). The combined organic extracts were washed with brine (2×100 mL), dried over MgSO4, filtered and concentrated to afford the desired product tert-butyl 4-cyano4-(6-methylpyridin-2-yl)piperidine-1-carboxylate (II-2) as a yellow-brown solid. Analytical LCMS: single peak (214 nm), 3.241 min. This product was used in next step reaction without further purification.

Workup

  1. extractionextracted with EtOAc (3×150 mL)
  2. washThe combined organic extracts were washed with brine (2×100 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5c5723485e2f43339bc8f87c5957df9b
Source dataset
uspto-grants-2010_11
Patent number
US07825135B2

Reaction notes

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