1,2-Diaminocyclohexane → [1-(4-chloro-phenyl)-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl]-acetic acid methyl ester

HRID 1260608ノート

反応式

HRID 1260608 の反応式
[CH3:1][O:2][C:3](=[O:15])[CH2:4][C:5]1[C:13]2[C:8](=[N:9][CH:10]=[CH:11][CH:12]=2)[NH:7][C:6]=1[CH3:14].[Cl:16][C:17]1[CH:22]=[CH:21][C:20](I)=[CH:19][CH:18]=1.C1(N)CCCCC1N.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CCOC(C)=O.[Cu]I.O1CCOCC1>[CH3:1][O:2][C:3](=[O:15])[CH2:4][C:5]1[C:13]2[C:8](=[N:9][CH:10]=[CH:11][CH:12]=2)[N:7]([C:20]2[CH:21]=[CH:22][C:17]([Cl:16])=[CH:18][CH:19]=2)[C:6]=1[CH3:14]

参加物

8

反応物 4

HCID 46101,2-DiaminocyclohexaneHCID 125101-Chloro-4-iodobenzeneHCID 62657Potassium Phosphate, TribasicHCID 67218699methyl 2-(2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)acetate

生成物 1

HCID 67220030[1-(4-chloro-phenyl)-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl]-acetic acid methyl ester

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
160 °C

実験手順

A mixture of (2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-acetic acid methyl ester (100 mg, 0.49 mmol), 1-chloro-4-iodo-benzene (117 mg, 0.49 mmol), CuI (5 mg, 0.03 mmol), cyclohexane-1,2-diamine (6 μL, 0.05 mmol), potassium phosphate (218 mg, 1.0 mmol) and 1,4-dioxane (0.5 mL) is heated at 160° C. for 140 minutes. The reaction is cooled, diluted with EtOAc, filtered through silica and evaporated to dryness. The residue is purified by flash column chromatography (5:1 iso-hexane/EtOAc elution) to furnish [1-(4-chloro-phenyl)-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl]-acetic acid methyl ester; MH+=315.

後処理

  1. temperatureThe reaction is cooled
  2. filtrationfiltered through silica
  3. customevaporated to dryness
  4. customThe residue is purified by flash column chromatography (5:1 iso-hexane/EtOAc elution)

出典と根拠

ORDレコード
ord-bd4c04ba9b6a45ec9ff5ab601e0e9aaa
出典データセット
uspto-grants-2013_06
特許番号
US08470848B2

反応ノート

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