(Prop-2-en-1-yl)stannane → 5-Allyl-4-chloro-2-[2-(3,5-dimethylphenyl)-acetylamino]-benzoic acid methyl ester

HRID 1858085Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:24])[C:4]1[CH:9]=[C:8](I)[C:7]([Cl:11])=[CH:6][C:5]=1[NH:12][C:13](=[O:23])[CH2:14][C:15]1[CH:20]=[C:19]([CH3:21])[CH:18]=[C:17]([CH3:22])[CH:16]=1.[CH2:25]([Sn])[CH:26]=[CH2:27]>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>[CH3:1][O:2][C:3](=[O:24])[C:4]1[CH:9]=[C:8]([CH2:27][CH:26]=[CH2:25])[C:7]([Cl:11])=[CH:6][C:5]=1[NH:12][C:13](=[O:23])[CH2:14][C:15]1[CH:20]=[C:19]([CH3:21])[CH:18]=[C:17]([CH3:22])[CH:16]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a suspension of 4-chloro-2-[2-(3,5-dimethylphenyl)-acetylamino]-5-iodo-benzoic acid methyl ester (2.39 g in 12 mL N,N-dimethylformamide) and 0.183 g bis(triphenylphosphine)palladium(II) chloride was added 2.02 mL allyltin and the mixture heated to 100° C. on an oil bath. After 2 hours, the mixture was cooled, partitioned between ethyl acetate and water and the organic layer washed further with brine. Concentration of the dried (magnesium sulfate) organics and purification by flash chromatography on silica gel (hexane:ethyl acetate, 95:5; then 90:10) gave the title compound (1.4 g).

Workup

temperaturethe mixture was cooled
custompartitioned between ethyl acetate and water
washthe organic layer washed further with brine
dry with materialConcentration of the dried (magnesium sulfate) organics
custompurification by flash chromatography on silica gel (hexane

Sources & evidence

ORD record: ord-14550849a94441acb59c33daca9c6c9f
Source dataset: uspto-grants-2000_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06150352

Reaction notes

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