2-Bromonaphthalene → 1-(4-Cyclopropylpyridin-3-yl)-3-(naphthalen-2-yl)imidazolidin-2-one

HRID 523530

反応式

HRID 523530 の反応式
[CH:1]1([C:4]2[CH:9]=[CH:8][N:7]=[CH:6][C:5]=2[N:10]2[CH2:14][CH2:13][NH:12][C:11]2=[O:15])[CH2:3][CH2:2]1.Br[C:17]1[CH:26]=[CH:25][C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=1.CN[C@@H]1CCCC[C@H]1NC.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.O1CCOCC1>[CH:1]1([C:4]2[CH:9]=[CH:8][N:7]=[CH:6][C:5]=2[N:10]2[CH2:14][CH2:13][N:12]([C:17]3[CH:26]=[CH:25][C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[CH:18]=3)[C:11]2=[O:15])[CH2:3][CH2:2]1

参加物

7

反応物 4

HCID 113722-BromonaphthaleneHCID 62657Potassium Phosphate, TribasicHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 709820071-(4-Cyclopropylpyridin-3-yl)imidazolidin-2-one

生成物 1

HCID 665764831-(4-Cyclopropylpyridin-3-yl)-3-(naphthalen-2-yl)imidazolidin-2-one収率 12%

試薬・触媒・溶媒 2

HCID 83717Copper iodide触媒HCID 312751,4-Dioxane溶媒

実験手順

Using analogous reagents and reaction conditions as described in Example 1 above, 1-(4-cyclopropylpyridin-3-yl)imidazolidin-2-one (I-1d: 70 mg, 0.344 mmol) was reacted with 2-bromonaphthalene (85.68 mg, 0.413 mmol), 1,4-dioxane (5 mL), copper iodide (6.5 mg, 0.034 mmol), trans-N,N′-dimethylcyclohexane-1,2-diamine (4.8 mg, 0.034 mmol) and potassium phosphate (219 mg, 1.034 mmol) to afford the crude product. Purification by column chromatography on silica gel (2% methanol in CHCl3), followed by preparative HPLC afforded 13 mg of the product (12% yield).

後処理

  1. customreagents and reaction conditions
  2. customto afford the crude product
  3. customPurification by column chromatography on silica gel (2% methanol in CHCl3)

出典と根拠

ORDレコード
ord-0ce33e7c7a094c4ca70ba06272843160
出典データセット
uspto-grants-2016_05
特許番号
US09339501B2

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