Sodium hydride → Ethyl 1-(2-tert-butoxy-2-oxoethyl)-4-(2-fluoro-4-iodoanilino)-6-oxo-1,6-dihydro-3-pyridinecarboxylate

HRID 917723Notes

Reaction equation

HRID 917723 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+].[C:24]([O:28][C:29](=[O:32])[CH2:30]Br)([CH3:27])([CH3:26])[CH3:25]>CN(C=O)C>[C:24]([O:28][C:29](=[O:32])[CH2:30][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)([CH3:27])([CH3:26])[CH3:25]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 23630800Ethyl 4-(2-fluoro-4-iodoanilino)-6-oxo-1,6-dihydro-3-pyridinecarboxylate

Product 1

HCID 23631094Ethyl 1-(2-tert-butoxy-2-oxoethyl)-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 t-butylbromoacetate 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 (1% MeOH/CH2Cl2 as eluant). Ethyl 1-(2-tert-butoxy-2-oxoethyl)-4-(2-fluoro-4-iodoanilino)-6-oxo-1,6-dihydro-3-pyridinecarboxylate was isolated as a white solid (72%), m.p. (EtOAc/hexanes) 149-151° C. 1H NMR [(CD3)2SO, 400 MHz] δ 9.34 (s, 1H), 8.57 (s, 1H), 7.78 (dd, J=10.0, 1.9 Hz, 1H), 7.61 (dd, J=8.4, 1.0 Hz, 1H), 7.31 (t, J=8.5 Hz, 1H), 5.43 (d, J=1.2 Hz, 1H), 4.62 (s, 2H), 4.31 (q, J=7.1 Hz, 2H), 1.42 (s, 9H), 1.33 (t, J=7.1 Hz, 3H). Anal Calcd for C20H22FIN2O5: C, 46.5; H, 4.3; N, 5.4. Found: C, 46.7; H, 4.2; N, 5.5.

Workup

  1. customto give a crude solid which
  2. customwas purified by column chromatography on silica gel (1% MeOH/CH2Cl2 as eluant)

Sources & evidence

ORD record
ord-96df00ab12044a69a724233aa2240a42
Source dataset
uspto-grants-2007_09
Patent number
US07273877B2

Reaction notes

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