Hexamethylphosphoramide → Ethyl 1-cyclopropyl-6-fluoro-7-[2,6-di(trifluoromethyl)-4-pyridinyl]-1,4-dihydro-4-oxo-3-quinolinecarboxylate

HRID 1681202Notes

Reaction equation

HRID 1681202 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:18])[C:7]([C:15]([O-:17])=[O:16])=[CH:8][N:9]2[CH:12]2[CH2:14][CH2:13]2)=[CH:4][C:3]=1[F:19].[F:20][C:21]([F:37])([F:36])[C:22]1[CH:27]=[C:26]([Sn](C)(C)C)[CH:25]=[C:24]([C:32]([F:35])([F:34])[F:33])[N:23]=1.CN(P(N(C)C)(N(C)C)=O)C.O1CCO[CH2:51][CH2:50]1>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH:12]1([N:9]2[C:10]3[C:5](=[CH:4][C:3]([F:19])=[C:2]([C:26]4[CH:27]=[C:22]([C:21]([F:37])([F:36])[F:20])[N:23]=[C:24]([C:32]([F:35])([F:34])[F:33])[CH:25]=4)[CH:11]=3)[C:6](=[O:18])[C:7]([C:15]([O:17][CH2:50][CH3:51])=[O:16])=[CH:8]2)[CH2:14][CH2:13]1

Participants

6

Reactant 4

HCID 12679HexamethylphosphoramideHCID 312751,4-DioxaneHCID 15030321HCID 15030321, compoundHCID 198072507-Bromo-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate

Product 1

HCID 15030322Ethyl 1-cyclopropyl-6-fluoro-7-[2,6-di(trifluoromethyl)-4-pyridinyl]-1,4-dihydro-4-oxo-3-quinolinecarboxylate

Reagents, catalysts & solvents 1

HCID 178418476HCID 178418476, compoundCatalyst

Procedure

Ethyl 1-cyclopropyl-6-fluoro-7-[2,6-di(trifluoromethyl)-4-pyridinyl]-1,4-dihydro-4-oxo-3-quinolinecarboxylate was prepared from 4 g 7-bromo-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate, 5 g 2,6-di(trifluoromethyl)-4-(trimethylstannyl)pyridine, 400 mg dichlorobis(triphenylphosphine)palladium and 2 ml HMPA in 60 ml dioxane according to the procedure of Example 1, part (h), and was obtained (2.8 g) as a solid with m.p. 239°-241° C.

Workup

  1. customwas obtained (2.8 g) as a solid with m.p. 239°-241° C.

Sources & evidence

ORD record
ord-dd9f476194904d81b184b887f82ef57a
Source dataset
uspto-grants-1992_12
Patent number
US05169853

Reaction notes

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