Triethylamine → N-(3-(2-chlorophenyl)-1-methyl-4-(phenylethynyl)-1H-pyrazol-5-yl)acetamide

HRID 1525379Notes

Reaction equation

[C:1]1([C:7]#[CH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCN(CC)CC.[Cl:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:23]1[C:27](I)=[C:26]([NH:29][C:30](=[O:32])[CH3:31])[N:25]([CH3:33])[N:24]=1>CN(C=O)C.[Cu]I.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>[Cl:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:23]1[C:27]([C:8]#[C:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[C:26]([NH:29][C:30](=[O:32])[CH3:31])[N:25]([CH3:33])[N:24]=1

Participants

Conditions

Temperature: 85 °C

Procedure

To a degassed solution of phenylacetylene (157 μl, 1.43 mmol) and Et3N (3.3 mL) in DMF (1.2 mL) were added N-(3-(2-chlorophenyl)-4-iodo-1-methyl-1H-pyrazol-5-yl)acetamide (413 mg, 1.1 mmol), CuI (42 mg, 0.22 mmol) and PdCl2(PPh3)2 (77 mg, 0.11 mmol). The mixture was flushed with N2 and then heated to 85° C. for 3 h. The reaction mixture was concentrated in metro and the residue was purified by column chromatography (silica gel, gradient 0 to 100% ethyl acetate/isohexane) yielding N-(3-(2-chlorophenyl)-1-methyl-4-(phenylethynyl)-1H-pyrazol-5-yl)acetamide as a solid (181 mg).

Workup

customThe mixture was flushed with N2
concentrationThe reaction mixture was concentrated in metro
customthe residue was purified by column chromatography (silica gel, gradient 0 to 100% ethyl acetate/isohexane)

Sources & evidence

ORD record: ord-bcfe1272b54a44d7810d90f0b5e15f4c
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09079909B2

Reaction notes

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