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Methyl chloroformate → [3-(1-Ethyl-5-fluoro-indan-1-yl)-1H-indol-7-yl]-carbamic acid methyl ester

HRID 13713
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HRID 13713 반응식
[CH2:1]([C:3]1([C:13]2[C:21]3[C:16](=[C:17]([NH2:22])[CH:18]=[CH:19][CH:20]=3)[NH:15][CH:14]=2)[C:11]2[C:6](=[CH:7][C:8]([F:12])=[CH:9][CH:10]=2)[CH2:5][CH2:4]1)[CH3:2].Cl[C:24]([O:26][CH3:27])=[O:25]>N1C=CC=CC=1.CCOCC>[CH3:27][O:26][C:24](=[O:25])[NH:22][C:17]1[CH:18]=[CH:19][CH:20]=[C:21]2[C:16]=1[NH:15][CH:14]=[C:13]2[C:3]1([CH2:1][CH3:2])[C:11]2[C:6](=[CH:7][C:8]([F:12])=[CH:9][CH:10]=2)[CH2:5][CH2:4]1
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참가 물질

5

반응물 2

HCID 6586Methyl chloroformateHCID 589417073-(1-Ethyl-5-fluoro-indan-1-yl)-1H-indol-7-ylamine

생성물 1

HCID 58941708[3-(1-Ethyl-5-fluoro-indan-1-yl)-1H-indol-7-yl]-carbamic acid methyl ester수율 36%

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 3283Diethyl Ether용매

실험 절차

Dissolve 3-(1-ethyl-5-fluoro-indan-1-yl)-1H-indol-7-ylamine (0.35 g, 1.19 mmol) in pyridine (3 ml). Add methyl chloroformate (0.10 ml, 1.31 mmol, 1.1 equivalents) and stir at room temperature under nitrogen overnight. Dilute with ether, wash with 1N aqueous hydrochloric acid (2×), dry over anhydrous sodium sulfate, filter, and concentrate solution in vacuo. Purify the residue on silica eluting with 0 to 75% ethyl acetate/hexanes over 30 minutes to provide the title compound as a white solid (0.15 g, 36%). LC-MS m/z 353.1 (M++1).

후처리

  1. washwash with 1N aqueous hydrochloric acid (2×)
  2. dry with materialdry over anhydrous sodium sulfate
  3. filtrationfilter
  4. concentrationconcentrate solution in vacuo
  5. customPurify the residue on silica eluting with 0 to 75% ethyl acetate/hexanes over 30 minutes

출처 및 근거

ORD 기록
ord-71866f818b4e40e097b0c842d5917d59
출처 데이터셋
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07728150B2

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