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

HRID 1768186Notes

Reaction equation

HRID 1768186 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][N:3]=1.C(N(CC)CC)C.[CH3:16][C:17]([CH3:22])([CH3:21])[C:18](Cl)=[O:19].C([O-])(O)=O.[Na+]>ClCCl.CN(C1C=CN=CC=1)C>[F:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:18](=[O:19])[C:17]([CH3:22])([CH3:21])[CH3:16])=[N:3][CH:4]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 516892Sodium BicarbonateHCID 27377012-Amino-5-fluoropyridine

Product 1

HCID 22293237N-(5-Fluoropyridin-2-yl)pivalamideYield 76.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a 0° C. solution of 2-amino-5-fluoropyridine (1.00 g, 8.92 mmol) and triethylamine (1.35 g, 13.4 mmol) in dichloromethane (30 mL) was added trimethylacetyl chloride (1.29 g, 10.7 mmol) and DMAP (0.11 g, 0.89 mmol). The solution was allowed to warm to room temperature. After 4 h, saturated aqueous NaHCO3 was added, the layers separated and the aqueous phase backwashed with DCM. The combined organics were dried over magnesium sulfate, filtered and concentrated and the residue purified by silica gel chromatography (5%→40% EtOAc/hexanes) to give the title compound (1.34 g). MS 197.3 (M+1).

Workup

  1. customthe layers separated
  2. dry with materialThe combined organics were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customthe residue purified by silica gel chromatography (5%→40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-f708e4519d494d4993c968b13a552469
Source dataset
uspto-grants-2007_06
Patent number
US07235545B2

Reaction notes

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