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

HRID 1445575

반응식

HRID 1445575 반응식
[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]

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

반응 조건

온도
160 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-9ee7b8443d4044a793a0ca295ef8bff7
출처 데이터셋
uspto-grants-2010_02
특허 번호
US07666878B2

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