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

HRID 917727Notes

Reaction equation

HRID 917727 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][CH2:27][C:28]#[N:29]>CN(C=O)C>[C:28]([CH2:27][CH2:26][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)#[N:29]

Participants

5

Reactant 3

HCID 214124-BromobutyronitrileHCID 24758Sodium hydrideHCID 23630800Ethyl 4-(2-fluoro-4-iodoanilino)-6-oxo-1,6-dihydro-3-pyridinecarboxylate

Product 1

HCID 23630802Ethyl 1-(3-cyanopropyl)-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 4-bromobutyronitrile 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-(3-cyanopropyl)-4-(2-fluoro-4-iodoanilino)-6-oxo-1,6-dihydro-3-pyridinecarboxylate was isolated as a white solid (67%), m.p. (EtOAc) 157-159° C. 1H NMR [(CD3)2SO, 400 MHz] δ 9.30 (s, 1H), 8.51 (s, 1H), 7.77 (dd, J=10.1, 1.9 Hz, 1H), 7.61 (br d, J=8.4 Hz, 1H), 7.30 (t, J=8.5 Hz, 1H), 5.46 (s, 1H), 4.31 (q, J=7.1 Hz, 2H), 3.96 (t, J=7.2 Hz, 2H), 2.53 (t, J=7.2 Hz, 2H), 1.93 (pentet, J=7.2 Hz, 2H), 1.33 (t, J=7.1 Hz, 3H). Anal. Calcd for C18H17FIN3O3: C, 46.1; H, 3.7; N, 9.0. Found: C, 46.4; H, 3.6; N, 8.9.

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-93b4b90aa8c94929b025caa88f713ab2
Source dataset
uspto-grants-2007_09
Patent number
US07273877B2

Reaction notes

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