Triethylamine → Benzoic acid 2,3,6-trifluoro-pyridin-4-ylmethyl ester

HRID 426227Notes

Reaction equation

HRID 426227 reaction equation
Cl[C:2]1[C:3]([F:20])=[N:4][C:5]([F:19])=[C:6]([F:18])[C:7]=1[CH2:8][O:9][C:10](=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C>[Pd].C(O)C>[F:19][C:5]1[C:6]([F:18])=[C:7]([CH2:8][O:9][C:10](=[O:17])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:2]=[C:3]([F:20])[N:4]=1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 59184703Benzoic acid 3-chloro-2,5,6-trifluoro-pyridin-4-ylmethyl ester

Product 1

HCID 59184767Benzoic acid 2,3,6-trifluoro-pyridin-4-ylmethyl esterYield 85.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Benzoic acid 3-chloro-2,5,6-trifluoro-pyridin-4-ylmethyl ester (4.52 g, 15 mmol), anhydrous ethanol (50 ml), 10% palladium on carbon (500 mg), and triethylamine (2.5 ml, 18 mmol) were placed into a 500 ml bottle. The mixture was hydrogenated under hydrogen atmosphere (50 psi) for 1.5 hr. The reaction mixture was filtered through celite pad and the pad was washed with ethanol. The combined filtrate was evaporated in vacuo and the residue was purified by silica gel column chromatography (eluent, ether:hexane (1:15)) to afford 3.43 g (85%) of benzoic acid 2,3,6-trifluoro-pyridin-4-ylmethyl ester as a white solid. m.p. 73-76° C.; 1H NMR (200 MHz, CDCl3) δ 5.52 (2H, s), 6.95 (1H, m), 7.30-7.70 (3H, m), 8.09-8.15 (2H, m).

Workup

  1. customfor 1.5 hr
  2. filtrationThe reaction mixture was filtered through celite pad
  3. washthe pad was washed with ethanol
  4. customThe combined filtrate was evaporated in vacuo
  5. customthe residue was purified by silica gel column chromatography (eluent, ether:hexane (1:15))

Sources & evidence

ORD record
ord-3c8e0d5ac3ed4e4d94001b05d4a9f075
Source dataset
uspto-grants-2012_01
Patent number
US08106064B2

Reaction notes

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