indium(III)chloride → HCID 57855969, compound

HRID 2039634Notes

Reaction equation

HRID 2039634 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, 9.04 mmol) in 5 ml of dry THF under argon is cooled to −78° C. and then treated drop wise with methyl magnesium chloride (3M in THF, 9.1 ml, 27.12 mmol). The milky suspension is allowed to warm to room temperature and then added drop wise to a refluxing solution of bis(triphenylphosphine)palladium(II)dichloride (0.19 g, 0.27 mmol) and 6-Nitro-5-trifluoromethanesulfonyloxy-2-trifluoromethyl-quinoline-7-carboxylic acid methyl ester (4.05 g, 9.042 mmol) in 35 ml of dry THF. The mixture is refluxed under argon, monitoring by TLC. After reaction completion, the reaction mixture is concentrated in vacuo, and the residue taken up in diethyl ether and washed successively with dilute aqueous hydrochloric acid and brine. The diethyl ether phase is dried over anhydrous sodium sulphate, filtered, and concentrated in vacuo. The residue (2.9 g) is purified by flash column chromatography, eluting with 4:1 hexane:ethyl acetate. This gives 2.0 g (70%) of the title product as yellow crystals. 1H NMR (CDCl3, 400 MHz): δ ppm: 2.7 (s, 3H); 4.0 (s, 3H); 7.98 (d, 1H); 8.68 (d, 1H); 8.83 ppm (s, 1H). LC/MS: 315 (M+1)+

Workup

  1. temperatureto warm to room temperature
  2. temperatureThe mixture is refluxed under argon
  3. customAfter reaction completion
  4. concentrationthe reaction mixture is concentrated in vacuo
  5. washwashed successively with dilute aqueous hydrochloric acid and brine
  6. dry with materialThe diethyl ether phase is dried over anhydrous sodium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue (2.9 g) is purified by flash column chromatography
  10. washeluting with 4:1 hexane

Sources & evidence

ORD record
ord-02b6f1ee9928448d83c53840864bb475
Source dataset
uspto-grants-2013_11
Patent number
US08580785B2

Reaction notes

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