Triethylamine → N-(4-(phenylethynyl)-1H-pyrazol-5-yl)acetamide

HRID 2205760ノート

反応式

HRID 2205760 の反応式
I[C:2]1[CH:3]=[N:4][NH:5][C:6]=1[NH:7][C:8](=[O:10])[CH3:9].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.[C:37]1([C:43]#[CH:44])[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>[Pd].C(O)C.[Cu]I>[C:37]1([C:43]#[C:44][C:2]2[CH:3]=[N:4][NH:5][C:6]=2[NH:7][C:8](=[O:10])[CH3:9])[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

参加物

8

反応物 4

HCID 8471TriethylamineHCID 10821PhenylacetyleneHCID 11776TriphenylphosphineHCID 86717260N-(4-iodo-1H-pyrazol-5-yl)acetamide

生成物 1

HCID 86717261N-(4-(phenylethynyl)-1H-pyrazol-5-yl)acetamide

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 702Ethanol溶媒

実験手順

Nitrogen was bubbled through a suspension of N-(4-iodo-1H-pyrazol-5-yl)acetamide (30 g, 120 mmol), 10% palladium on carbon (50% water, 7.4 g, 3 mmol), copper(I) iodide (1.14 g, 6 mmol), triphenylphosphine (6.3 g, 24 mmol) and triethylamine (50 mL, 360 mmol) in ethanol (600 mL) for 20 min. Phenyl acetylene was added and nitrogen bubbled through the mixture for a further 25 min. The reaction mixture was then heated and stirred under reflux conditions in an atmosphere of nitrogen for 3 d and cooled to room temperature. The reaction mixture was filtered through celite and the filtrate was concentrated in vacuo. The residue was purified by column chromatography (silica gel, iso-hexanes/ethyl acetate 9:1 to 0:1) yielding the title compound as a solid (17.6 g).

後処理

  1. customnitrogen bubbled through the mixture for a further 25 min
  2. temperatureThe reaction mixture was then heated
  3. filtrationThe reaction mixture was filtered through celite
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe residue was purified by column chromatography (silica gel, iso-hexanes/ethyl acetate 9:1 to 0:1)

出典と根拠

ORDレコード
ord-6a59d13d32124affbf8511c0f34b1f02
出典データセット
uspto-grants-2016_06
特許番号
US09371332B2

反応ノート

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