Water → HCID 86595534, compound

HRID 2384370Notes

Reaction equation

[F:1][C:2]([F:28])([F:27])[C:3]1[CH:4]=[C:5]([NH:13][C:14](=[O:26])[C:15]2[CH:20]=[C:19](I)[CH:18]=[CH:17][C:16]=2[O:22][CH2:23][O:24][CH3:25])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.C([Sn](CCCC)(CCCC)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=1)CCC.O>CN(C)C=O.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>[F:1][C:2]([F:28])([F:27])[C:3]1[CH:4]=[C:5]([NH:13][C:14](=[O:26])[C:15]2[CH:20]=[C:19]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=3)[CH:18]=[CH:17][C:16]=2[O:22][CH2:23][O:24][CH3:25])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1

Participants

Conditions

Temperature: 100 °C

Procedure

N-[3,5-Bis(trifluoromethyl)phenyl]-5-iodo-2-methoxymethoxybenzamide (0.20 g, 0.39 mmol) was dissolved in N,N-dimethylformamide (8 ml). Tri-n-butyl(2-pyridyl)tin (0.13 ml, 0.41 mmol) and dichlorobis(triphenylphosphine)palladium(32.1 mg, 0.05 mmol) were added, and the mixture was stirred at 100° C. for 1.5 hours. After cooling, the reaction mixture was poured into water and extracted with ethyl acetate. After the organic layer was washed with water and brine, dried over anhydrous sodium sulfate, the residue obtained by evaporation under reduced pressure was purified by chromatography on silica gel (n-hexane:ethyl acetate=2:1→1:1) to give the title compound (37.9 mg, 20.8%) as a white powder.

Workup

temperatureAfter cooling
extractionextracted with ethyl acetate
washAfter the organic layer was washed with water and brine
dry with materialdried over anhydrous sodium sulfate
customthe residue obtained by evaporation under reduced pressure
customwas purified by chromatography on silica gel (n-hexane:ethyl acetate=2:1→1:1)

Sources & evidence

ORD record: ord-9646002da4064e0796de9576fee198f8
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08263657B2

Reaction notes

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