2-(p-Toluenesulfonyl)-5-tributylstannylisoindoline → HCID 15870841, compound

HRID 1584824Notes

Reaction equation

HRID 1584824 reaction equation
Br[C:2]1[C:11]([CH3:12])=[C:10]2[C:5]([C:6](=[O:21])[C:7]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:8][N:9]2[CH:13]2[CH2:15][CH2:14]2)=[CH:4][C:3]=1[F:22].[C:23]1([CH3:54])[CH:28]=[CH:27][C:26]([S:29]([N:32]2[CH2:40][C:39]3[C:34](=[CH:35][CH:36]=[C:37]([Sn](CCCC)(CCCC)CCCC)[CH:38]=3)[CH2:33]2)(=[O:31])=[O:30])=[CH:25][CH:24]=1>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:13]1([N:9]2[C:10]3[C:5](=[CH:4][C:3]([F:22])=[C:2]([C:36]4[CH:35]=[C:34]5[C:39](=[CH:38][CH:37]=4)[CH2:40][N:32]([S:29]([C:26]4[CH:27]=[CH:28][C:23]([CH3:54])=[CH:24][CH:25]=4)(=[O:31])=[O:30])[CH2:33]5)[C:11]=3[CH3:12])[C:6](=[O:21])[C:7]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:8]2)[CH2:15][CH2:14]1

Participants

5

Reactant 2

HCID 158708542-(p-Toluenesulfonyl)-5-tributylstannylisoindolineHCID 21220308HCID 21220308, compound

Product 1

HCID 15870841HCID 15870841, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

In 1 ml of toluene was suspended 47 mg of ethyl 7-bromo-1-cyclopropyl-6-fluoro-8-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylate, and to this suspension were added 74 mg of 2-(p-toluenesulfonyl)-5-tributylstannylisoindoline and 1.5 mg of tetrakis(triphenylphosphine)palladium (0), after which the resulting mixture was heated under reflux for 18 hours under a nitrogen atmosphere. The reaction mixture was concentrated under reduced pressure, and the residue obtained was purified by a column chromatography (eluent: n-hexane:ethyl acetate=1:1), and diethyl ether was then added thereto, after which the crystals formed were collected by filtration, to obtain 27 mg of colorless, crystalline ethyl 1-cyclopropyl-6-fluoro-8-methyl-7-[2-(p-toluenesulfonyl)isoindolin-5-yl]-1,4-dihydro-4-oxoquinoline-3-carboxylate.

Workup

  1. temperatureafter which the resulting mixture was heated
  2. temperatureunder reflux for 18 hours under a nitrogen atmosphere
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customthe residue obtained
  5. customwas purified by a column chromatography (eluent: n-hexane:ethyl acetate=1:1), and diethyl ether
  6. additionwas then added
  7. customafter which the crystals formed
  8. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-8800f2f5f56d4e2ab1947337aa3e271f
Source dataset
uspto-grants-1999_08
Patent number
US05935952

Reaction notes

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