Iodoethane → Ethyl 1-ethyl-4-(2-fluoro-4-iodoanilino)-6-oxo-1,6-dihydro-3-pyridinecarboxylate

HRID 917729Notes

Reaction equation

HRID 917729 reaction equation
[F:1][C:2]1[CH:20]=[C:19]([I:21])[CH:18]=[CH:17][C:3]=1[NH:4][C:5]1[C:6]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:7][NH:8][C:9](=[O:11])[CH:10]=1.[H-].[Na+].I[CH2:25][CH3:26]>CN(C=O)C>[CH2:25]([N:8]1[C:9](=[O:11])[CH:10]=[C:5]([NH:4][C:3]2[CH:17]=[CH:18][C:19]([I:21])=[CH:20][C:2]=2[F:1])[C:6]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:7]1)[CH3:26]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 23630800Ethyl 4-(2-fluoro-4-iodoanilino)-6-oxo-1,6-dihydro-3-pyridinecarboxylate

Product 1

HCID 23631095Ethyl 1-ethyl-4-(2-fluoro-4-iodoanilino)-6-oxo-1,6-dihydro-3-pyridinecarboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl 4-(2-fluoro-4-iodoanilino)-6-oxo-1,6-dihydro-3-pyridinecarboxylate was reacted with NaH and iodoethane in DMF under the same conditions as for example 22, step A to give a crude solid which was purified by column chromatography on silica gel (50% EtOAc/hexanes as eluant). Ethyl 1-ethyl-4-(2-fluoro-4-iodoanilino)-6-oxo-1,6-dihydro-3-pyridinecarboxylate was isolated as white needles (61%), m.p. (EtOAc/hexanes) 138-142° C. 1H NMR [(CD3)2SO, 400 MHz] δ 9.29 (s, 1H), 8.52 (s, 1H), 7.77 (dd, J=10.1, 1.9 Hz, 1H), 7.60 (ddd, J=8.4, 2.0, 0.8 Hz, 1H), 7.31 (t, J=8.5 Hz, 1H), 5.45 (s, 1H), 4.30 (q, J=7.1 Hz, 2H), 3.93 (q, J=7.1 Hz, 2H), 1.33 (t, J=7.1 Hz, 3H), 1.20 (t, J=7.1 Hz, 3H). Anal. Calcd for C16H16FIN2O3: C, 44.7; H, 3.8; N, 6.5. Found: C, 45.0; H, 3.6; N, 6.4.

Workup

  1. customto give a crude solid which
  2. customwas purified by column chromatography on silica gel (50% EtOAc/hexanes as eluant)

Sources & evidence

ORD record
ord-ea9f3f06e7a94a6098cd1e53c598d80e
Source dataset
uspto-grants-2007_09
Patent number
US07273877B2

Reaction notes

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