1-(4-Fluorophenyl)-4-oxo-7-(4-pyridyl)quinoline-3-carboxamide → 7-Chloro-1-(4-fluorophenyl)-4-oxo-quinoline-3-carboxamide

HRID 1032740Notes

Reaction equation

HRID 1032740 reaction equation
[Cl:1]C1C=C2C(C(=O)C(C(O)=O)=CN2C2C=CC=C(F)C=2)=CC=1.[F:23][C:24]1[CH:29]=[CH:28][C:27]([N:30]2[C:39]3[C:34](=[CH:35][CH:36]=[C:37](C4C=CN=CC=4)[CH:38]=3)[C:33](=[O:46])[C:32]([C:47]([NH2:49])=[O:48])=[CH:31]2)=[CH:26][CH:25]=1>>[Cl:1][C:37]1[CH:38]=[C:39]2[C:34]([C:33](=[O:46])[C:32]([C:47]([NH2:49])=[O:48])=[CH:31][N:30]2[C:27]2[CH:28]=[CH:29][C:24]([F:23])=[CH:25][CH:26]=2)=[CH:35][CH:36]=1

Participants

3

Reactant 2

HCID 4433701-(4-Fluorophenyl)-4-oxo-7-(4-pyridyl)quinoline-3-carboxamideHCID 103137647-Chloro-1,4-dihydro1-(3-fluorophenyl)-4-oxo-3-quinolinecarboxylic acid

Product 1

HCID 4787677-Chloro-1-(4-fluorophenyl)-4-oxo-quinoline-3-carboxamide

Procedure

7-Chloro-1,4-dihydro-1-(3-fluorophenyl)-4-oxo-3-quinolinecarboxamide [IV; R=H, R1 =3-FC6H4, R2 =H, R6H, X=Cl]was prepared from 7.36 g 7-chloro-1,4-dihydro1-(3-fluorophenyl)-4-oxo-3-quinolinecarboxylic acid by the procedure of Example 1, part (h), and was obtained (7.14 g) as a colorless solid, m.p. 294-296° C. when recrystallized from DMF. e) 1,4-Dihydro-1-(3-fluorophenyl)-4-oxo-7-(4-pyridinyl)3-quinolinecarboxamide [I; R=H, R1 =3-FC6H4, R2 =H, R6H, R7 4 -pyridinyl]was prepared from 4.13 g 7-chloro-1,4-dihydro-1-(3-fluorophenyl)-4-oxo-3-quinolinecarboxamide, 3.78 g 4-trimethylstannylpyridine and 0.46 g dichloro-bis-triphenylphosphine palladium according to the procedure of Example 37, part (c), and was obtained (2.4 g) in the form of its methanesulfonate salt, m.p. above 320° C. when recrystallized from methanol.

Workup

  1. customwas obtained (7.14 g) as a colorless solid, m.p. 294-296° C. when
  2. customrecrystallized from DMF
  3. customR=H, R1 =3-FC6H4, R2 =H, R6H, R7 4 -pyridinyl]was prepared from 4.13 g 7-chloro-1,4-dihydro-1-(3-fluorophenyl)-4-oxo-3-quinolinecarboxamide, 3.78 g 4-trimethylstannylpyridine and 0.46 g dichloro-bis-triphenylphosphine palladium according to the procedure of Example 37, part (c)

Sources & evidence

ORD record
ord-0008ae510c55413da06a7c754b4dc1ee
Source dataset
uspto-grants-1990_09
Patent number
US04959363

Reaction notes

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