indium(III)chloride → HCID 57855969, compound

HRID 887734Notes

Reaction equation

HRID 887734 reaction equation
[Cl-].[Cl-].[Cl-].[In+3].[CH3:5][Mg]Cl.[CH3:8][O:9][C:10]([C:12]1[CH:21]=[C:20]2[C:15]([CH:16]=[CH:17][C:18]([C:22]([F:25])([F:24])[F:23])=[N:19]2)=[C:14](OS(C(F)(F)F)(=O)=O)[C:13]=1[N+:34]([O-:36])=[O:35])=[O:11]>C1COCC1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[CH3:8][O:9][C:10]([C:12]1[CH:21]=[C:20]2[C:15]([CH:16]=[CH:17][C:18]([C:22]([F:25])([F:24])[F:23])=[N:19]2)=[C:14]([CH3:5])[C:13]=1[N+:34]([O-:36])=[O:35])=[O:11]

Participants

6

Reactant 3

HCID 159675indium(III)chlorideHCID 57855966HCID 57855966, compoundHCID 178418332HCID 178418332, compound

Product 1

HCID 57855969HCID 57855969, compound

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

A suspension of indium trichloride (2.0 g) in dry THF (5 mL) under an argon atmosphere is cooled to −78° C. and then treated drop wise with methyl magnesium chloride (9.1 mL, 3 M in THF). The milky suspension is allowed to warm to room temperature and then added drop wise to a refluxing solution of bis(triphenylphosphine)palladium(II)chloride (0.19 g) and 6-nitro-5-trifluoromethanesulfonyloxy-2-trifluoromethyl-quinoline-7-carboxylic acid methyl ester (4.05 g) in dry THF (35 mL). The mixture is refluxed under an argon atmosphere, monitoring by TLC. After reaction completion, the reaction mixture is concentrated in vacuum. The residue is taken up in diethyl ether and washed successively with diluted hydrochloric acid and brine. The diethyl ether phase is dried over anhydrous sodium sulfate, filtered and concentrated in vacuum. The residue is purified by column chromatography (hexane/ethyl acetate=4:1) to give 2.0 g of the title compound of the formula

Workup

  1. temperatureto warm to room temperature
  2. temperatureThe mixture is refluxed under an argon atmosphere
  3. customAfter reaction completion
  4. concentrationthe reaction mixture is concentrated in vacuum
  5. washwashed successively with diluted hydrochloric acid and brine
  6. dry with materialThe diethyl ether phase is dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuum
  9. customThe residue is purified by column chromatography (hexane/ethyl acetate=4:1)

Sources & evidence

ORD record
ord-75d6e32055fe412eb6b66dd5011d048f
Source dataset
uspto-grants-2012_08
Patent number
US08247431B2

Reaction notes

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