HCID 10315575, compound → HCID 22164813, compound

HRID 1032732Notes

Reaction equation

HRID 1032732 reaction equation
Cl[C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:24])[C:7]([C:19]([O:21][CH2:22][CH3:23])=[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.[CH3:25][N:26]1[CH:30]=[C:29]([Sn](C)(C)C)[S:28][CH2:27]1>C(O)C>[F:18][C:15]1[CH:14]=[CH:13][C:12]([N:9]2[C:10]3[C:5](=[CH:4][CH:3]=[C:2]([C:29]4[S:28][CH2:27][N:26]([CH3:25])[CH:30]=4)[CH:11]=3)[C:6](=[O:24])[C:7]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:8]2)=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 10315575HCID 10315575, compoundHCID 22164812HCID 22164812, compound

Product 1

HCID 22164813HCID 22164813, compoundYield 51.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4.34 g ethyl 7-chloro-1,4-dihydro1-(4-fluorophenyl)-4-oxo-3-quinolinecarboxylate, 6.55 g 3-methyl-5-trimethylstannylthiazole and 1.52 g dichloro- bis-triphenylphosphine palladium in 150 ml absolute ethanol was heated at 150° C. in a stirred stainless steel bomb for about 16 hrs. The product was isolated and chromatographed on silica gel. Elution with 1:1 ethyl acetate/hexane and 100% ethyl acetate gave 2.67 g ethyl 1,4-dihydro-1-(4-fluorophenyl)-7-(3-methyl-5-thiazolyl)-4- oxo-3-quinolinecarboxylate as a yellow solid.

Workup

  1. customThe product was isolated
  2. customchromatographed on silica gel
  3. washElution with 1:1 ethyl acetate/hexane and 100% ethyl acetate

Sources & evidence

ORD record
ord-97a5b7f3ac8b4a12b9c388c3bdc4dbaf
Source dataset
uspto-grants-1990_09
Patent number
US04959363

Reaction notes

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