1-Ethyl-7-isoxazol-5-yl-4-oxo-quinoline-3-carboxamide → 1-(4-Fluorophenyl)-4-oxo-7-phenyl-quinoline-3-carboxamide

HRID 1032738Notes

Reaction equation

HRID 1032738 reaction equation
Cl[C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:22])[C:7]([C:19]([NH2:21])=[O:20])=[CH:8][N:9]2[C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)=[CH:4][CH:3]=1.C([Sn]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)(CCCC)CCCC)CCC.C(N1C2C(=CC=C(C3ON=CC=3)C=2)C(=O)C(C(N)=O)=C1)C>>[F:18][C:15]1[CH:16]=[CH:17][C:12]([N:9]2[C:10]3[C:5](=[CH:4][CH:3]=[C:2]([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)[CH:11]=3)[C:6](=[O:22])[C:7]([C:19]([NH2:21])=[O:20])=[CH:8]2)=[CH:13][CH:14]=1

Participants

4

Reactant 3

HCID 4787261-Ethyl-7-isoxazol-5-yl-4-oxo-quinoline-3-carboxamideHCID 4787677-Chloro-1-(4-fluorophenyl)-4-oxo-quinoline-3-carboxamideHCID 607632Tributylphenyltin

Product 1

HCID 4787231-(4-Fluorophenyl)-4-oxo-7-phenyl-quinoline-3-carboxamide

Procedure

1,4-Dihydro-1-(4-fluorophenyl)-4-oxo-7-phenyl-3-quinolinecarboxamide [I; R=H, R1 =4-FC6H4, R2 =H, R6 =H, R7C6H5 ] was prepared from 2.22 g 1,4-dihydro-7-chloro1-(4-fluorophenyl)-4-oxo-3-quinolinecarboxamide (Example 42c), 3.30 g tributylstannylbenzene (prepared from tributyltin chloride and bromobenzene) and 2.50 g dichlorobis-triphenylphosphine palladium according to the procedure of Example 37, part (c), and was obtained (1.4 g) as colorless crystals, m.p. 289-292° C. when recrystallized from acetonitrile.

Workup

  1. customwas obtained (1.4 g) as colorless crystals, m.p. 289-292° C. when
  2. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-f4c8945dbacf47eb803ccd497322e27d
Source dataset
uspto-grants-1990_09
Patent number
US04959363

Reaction notes

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