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

HRID 917731Notes

Reaction equation

HRID 917731 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+].Br[CH2:25][CH2:26][CH3:27]>CN(C=O)C>[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][N:8]([CH2:25][CH2:26][CH3:27])[C:9](=[O:11])[CH:10]=1

Participants

5

Reactant 3

HCID 78401-BromopropaneHCID 24758Sodium hydrideHCID 23630800Ethyl 4-(2-fluoro-4-iodoanilino)-6-oxo-1,6-dihydro-3-pyridinecarboxylate

Product 1

HCID 23630803Ethyl 4-(2-fluoro-4-iodoanilino)-6-oxo-1-propyl-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 bromopropane 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 4-(2-fluoro-4-iodoanilino)-6-oxo-1-propyl-1,6-dihydro-3-pyridinecarboxylate was isolated as a white solid (54%), m.p. (EtOAc/hexanes) 147-150° C. 1H NMR [(CD3)2SO, 400 MHz] δ 9.29 (s, 1H), 8.50 (s, 1H), 7.76 (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), 5.46 (d, J=1.3 Hz, 1H), 4.30 (q, J=7.1 Hz, 2H), 3.85 (t, J=7.3 Hz, 2H), 1.62 (sextet, J=7.3 Hz, 2H), 1.33 (t, J=7.1 Hz, 3H), 0.85 (t, J=7.4 Hz, 3H). Anal. Calcd for C17H18FIN2O3: C, 46.0; H, 4.1; N, 6.3. Found: C, 45.8; H, 3.9; N, 6.0.

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-0e7585bc02c6455798022e7f7442a42c
Source dataset
uspto-grants-2007_09
Patent number
US07273877B2

Reaction notes

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