Triethylamine → 4-Hydroxy-3-methoxy-n-[3-[2-(2-trifluoromethylphenyl)ethynyl]phenyl]phenylacetamide

HRID 7067

Reaction equation

[C:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10](=[O:21])[CH2:11][C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([O:19][CH3:20])[CH:13]=2)[CH:6]=[CH:7][CH:8]=1)#[CH:2].[F:22][C:23]([F:32])([F:31])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1I.C(N(CC)CC)C>[Cu]I.C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(#N)C>[OH:18][C:15]1[CH:16]=[CH:17][C:12]([CH2:11][C:10]([NH:9][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:1]#[C:2][C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=3[C:23]([F:32])([F:31])[F:22])[CH:4]=2)=[O:21])=[CH:13][C:14]=1[O:19][CH3:20]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of N-(3-ethynylphenyl)-4-hydroxy-3-methoxypheny-acetamide (the compound of Example 19) (200 mg), 1-trifluoromethyl-2-iodobenzene (280 mg), copper (I) iodide (19 mg), bis(triphenylphosphine)palladium (II) dichloride (70 mg), triethylamine (1 g) and acetonitrile (3 ml) is heated with stirring at 50° C. under argon atmosphere for 18 hours. The solvent is evaporated under reduced pressure, and the residue is purified by silica gel column chromatography (eluent: gradient from 0% to 100% hexane/ethyl acetate) to give the desired compound (120 mg).

Workup

temperatureis heated
customThe solvent is evaporated under reduced pressure
customthe residue is purified by silica gel column chromatography (eluent: gradient from 0% to 100% hexane/ethyl acetate)

Sources & evidence

ORD record: ord-b5a3ba4d153e4ab996f6b3ba98b5134c
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07084176B2

Linked notes

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