6-Ethylsulfanyl-5-fluoro-2-(4-methoxy-benzylamino)-nicotinic acid ethyl ester → 5-Fluoro-2-(4-methoxy-benzylamino)-nicotinic acid ethyl ester

HRID 901248Notes

Reaction equation

HRID 901248 reaction equation
[CH2:1]([O:3][C:4](=[O:25])[C:5]1[CH:10]=[C:9]([F:11])[C:8](SCC)=[N:7][C:6]=1[NH:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1)[CH3:2]>[Ni].C(O)C>[CH2:1]([O:3][C:4](=[O:25])[C:5]1[CH:10]=[C:9]([F:11])[CH:8]=[N:7][C:6]=1[NH:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1)[CH3:2]

Participants

4

Reactant 1

HCID 596996366-Ethylsulfanyl-5-fluoro-2-(4-methoxy-benzylamino)-nicotinic acid ethyl ester

Product 1

HCID 589458085-Fluoro-2-(4-methoxy-benzylamino)-nicotinic acid ethyl esterYield 93%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

Freshly activated raney nickel (50 g) was added to a solution of 6-ethylsulfanyl-5-fluoro-2-(4-methoxy-benzylamino)-nicotinic acid ethyl ester (67) (31 g, 85 mmol) in anhydrous ethanol and refluxed for 48 h. The solution was cooled and filtered through celite. The filtrate was evaporated under reduced pressure to yield 24 g (93%) of 5-fluoro-2-(4-methoxy-benzylamino)-nicotinic acid ethyl ester (68) as a viscous oil which solidified to a white solids after keeping several days under vacuum at room temperature. Mp 90° C. 1H-NMR (DMSO-d6): δ 1.30 (t, J=7.2 Hz, 3H), 3.71 (s, 3H), 4.29 q, J=7.2 Hz, 2H), 4.55 (d, J=5.6 Hz, 2H), 6.87 (m, 2H), 7.26 (m, 2H), 7.96 (dd, J=3.2, 8.8 Hz, 1H), 8.12 (m, 1H), 8.35 (d, J=3.2 Hz, 1H); EIMS m/z 305 (M+1).

Workup

  1. temperaturerefluxed for 48 h
  2. temperatureThe solution was cooled
  3. filtrationfiltered through celite
  4. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-3db86a7e30ac4d91b8f31d3b0b0ae3ae
Source dataset
uspto-grants-2008_04
Patent number
US07361760B2

Reaction notes

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