Methane → N-(5-Fluoropyridin-2-yl)pivalamide

HRID 1272167Notes

Reaction equation

HRID 1272167 reaction equation
C(N(CC)CC)C.[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][N:10]=1.[C:16](Cl)(=[O:21])[C:17]([CH3:20])([CH3:19])[CH3:18].C>ClCCl>[F:15][C:12]1[CH:13]=[CH:14][C:9]([NH:8][C:16](=[O:21])[C:17]([CH3:20])([CH3:19])[CH3:18])=[N:10][CH:11]=1

Participants

6

Reactant 4

HCID 297MethaneHCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 27377012-Amino-5-fluoropyridine

Product 1

HCID 22293237N-(5-Fluoropyridin-2-yl)pivalamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 33.6 mL triethylamine and 22.5 2-amino-5-fluoropyridine (0.201 mol) in 200 mL dichloromethane was added dropwise a solution of 28 mL pivaloyl chloride (0.201 mol) in 50 mL dichloromethane at such a rate that the temperature did not exceed 15° C. (ice bath cooling). The mixture was then stirred overnight with thawing to room temperature. To the resulting brown-black suspension was added 5 g charcoal and the mixture was stirred at room temperature for 30 min and filtered through dicalite. The orange- yellow mother liquor was purified by filtration over a layer of silica gel (400 g) with heptane:ethyl acetate=4:1. The slightly yellow product fractions were evaporated and the oily residue was distilled in a kugelrohr apparatus at 100° C. and 0.5 mbar. The compound crystallized on standing at room temperature.

Workup

  1. customdid not exceed 15° C.
  2. temperature(ice bath cooling)
  3. stirringthe mixture was stirred at room temperature for 30 min
  4. filtrationfiltered through dicalite
  5. filtrationThe orange- yellow mother liquor was purified by filtration over a layer of silica gel (400 g) with heptane
  6. customThe slightly yellow product fractions were evaporated
  7. distillationthe oily residue was distilled in a kugelrohr apparatus at 100° C.
  8. customThe compound crystallized
  9. customon standing at room temperature

Sources & evidence

ORD record
ord-351559b72cab45eeb0bd189c27c6344c
Source dataset
uspto-grants-2007_04
Patent number
US07208494B2

Reaction notes

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