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

HRID 1255395Notes

Reaction equation

HRID 1255395 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.[C:16](Cl)(=[O:21])[C:17]([CH3:20])([CH3:19])[CH3:18]>ClCCl>[F:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:16](=[O:21])[C:17]([CH3:20])([CH3:19])[CH3:18])=[N:3][CH:4]=1

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-amino-5-fluoropyridine (50.0 g, commercially available) and triethylamine (93 ml) in dichloromethane (600 ml) was added pivaloyl chloride (56 ml) at ambient temperature. The slurry that formed was stirred for 3 hours, stored for 18 hours then washed with water (200 ml), brine (100 ml) then dried over magnesium sulfate, filtered and evaporated under reduced pressure to give the required product as a brown oil, 86 g. 1H NMR (CDCl3) δ: 8.30 (1H, dd), 8.10 (1H, d), 8.00 (1H, bs), 7.42 (1H, m), 1.30 (9H, s).

Workup

  1. customThe slurry that formed
  2. waitstored for 18 hours
  3. washthen washed with water (200 ml), brine (100 ml)
  4. dry with materialthen dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-f6d4e68200024c41a5e3532af40aa233
Source dataset
uspto-grants-2013_06
Patent number
US08461083B2

Reaction notes

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