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Diiodomethane → HCID 67172047, 화합물

HRID 450110
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HRID 450110 반응식
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([C:10]2[CH2:11][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:13][CH:14]=2)=[CH:2]1.[CH2:22]([Zn]CC)C.ICI>C(Cl)Cl.CCCCCC>[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([C:10]23[CH2:22][CH:14]2[CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11]3)=[CH:2]1
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참가 물질

6

반응물 3

HCID 6346DiiodomethaneHCID 67172412HCID 67172412, 화합물HCID 178418750HCID 178418750, 화합물

생성물 1

HCID 67172047HCID 67172047, 화합물

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8058Hexane용매

실험 절차

To a solution of tert-butyl 3-(1H-pyrrolo[2,3-b]pyridin-3-yl)-2,5-dihydro-1H-pyrrole-1-carboxylate (700 mg, 2.5 mmol) in DCM (20 mL), was added dropwise at 0° C. under nitrogen atmosphere diethylzinc (6.13 mL of a 1M solution in hexane, 6.1 mmol) and diiodomethane (0.79 mL, 9.8 mmol). The mixture was warmed to RT and stirred at RT overnight. The mixture was then cooled with an ice bath and quenched with a saturated aqueous solution of ammonium chloride. The mixture was extracted with DCM, dried over sodium sulphate and concentrated in vacuo. The residue was triturated in diisopropylether and the resulting precipitate was filtered and then purified by column chromatography (DCM/MeOH 95:5) to afford the title compound as a yellow solid (100 mg).

후처리

  1. temperatureThe mixture was then cooled with an ice bath
  2. customquenched with a saturated aqueous solution of ammonium chloride
  3. extractionThe mixture was extracted with DCM
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated in vacuo
  6. customThe residue was triturated in diisopropylether
  7. filtrationthe resulting precipitate was filtered
  8. custompurified by column chromatography (DCM/MeOH 95:5)

출처 및 근거

ORD 기록
ord-cdca724b877c49808d90dc0610d91e65
출처 데이터셋
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08486964B2

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