HCID 60026398, compound → HCID 60026332, compound

HRID 400664Notes

Reaction equation

HRID 400664 reaction equation
[C:1]([C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[C:6](OS(C(F)(F)F)(=O)=O)=[C:5]([CH3:20])[CH:4]=1)#[N:2].[CH3:21][S:22]([C:25]1[CH:26]=[C:27]([C:34]([CH3:46])([CH3:45])[CH2:35][C:36]([C:41]([F:44])([F:43])[F:42])([OH:40])[CH2:37][C:38]#[CH:39])[C:28]2[O:32][CH2:31][CH2:30][C:29]=2[CH:33]=1)(=[O:24])=[O:23]>C1(C)C=CC=CC=1.C(N(CC)CC)C.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.[Cu]I>[OH:40][C:36]([C:41]([F:43])([F:44])[F:42])([CH2:35][C:34]([C:27]1[C:28]2[O:32][CH2:31][CH2:30][C:29]=2[CH:33]=[C:25]([S:22]([CH3:21])(=[O:24])=[O:23])[CH:26]=1)([CH3:45])[CH3:46])[CH2:37][C:38]#[C:39][C:6]1[C:7]([N+:9]([O-:11])=[O:10])=[CH:8][C:3]([C:1]#[N:2])=[CH:4][C:5]=1[CH3:20]

Participants

7

Reactant 2

HCID 60026398HCID 60026398, compoundHCID 86040733HCID 86040733, compound

Product 1

HCID 60026332HCID 60026332, compoundYield 43%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 1140TolueneSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of trifluoromethanesulfonic acid 4-cyano-2-methyl-6-nitrophenyl ester (217 mg, 0.7 mmol), dichlorobis(triphenylphosphine)palladium (II) (24.6 mg, 0.035 mmol), copper (I) iodide (13.3 mg, 0.7 mmol), and 6-(5-methanesulfonyl-2,3-dihydrobenzofuran-7-yl)-6-methyl-4-trifluoromethylhept-1-yn-4-ol (273 mg, 0.7 mmol) in a mixture of 0.8 mL of anhydrous toluene and 0.3 mL of anhydrous triethylamine was heated in a microwave at 60° C. for 10 minutes. The reaction mixture was applied to a column of SiO2 (50% ethyl acetate in hexanes) to give 165 mg of the title product as a light yellow oil (43% yield).

Sources & evidence

ORD record
ord-5c818b4ee13e4d7b80a9914bb5d2183d
Source dataset
uspto-grants-2014_06
Patent number
US08741897B2

Reaction notes

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