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Tributylphosphine → Ethyl 5-[4-(methylsulfonyl)phenoxy]-7-(tetrahydro-2H-pyran-4-ylmethoxy)-1H-indole-2-carboxylate

HRID 1188884
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HRID 1188884 반응식
[OH:1][C:2]1[CH:3]=[C:4]([O:16][C:17]2[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:19][CH:18]=2)[CH:5]=[C:6]2[C:10]=1[NH:9][C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7]2.[O:27]1[CH2:32][CH2:31][CH:30]([CH2:33]O)[CH2:29][CH2:28]1.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.C(P(CCCC)CCCC)CCC>O1CCCC1>[CH3:26][S:23]([C:20]1[CH:21]=[CH:22][C:17]([O:16][C:4]2[CH:5]=[C:6]3[C:10](=[C:2]([O:1][CH2:33][CH:30]4[CH2:31][CH2:32][O:27][CH2:28][CH2:29]4)[CH:3]=2)[NH:9][C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7]3)=[CH:18][CH:19]=1)(=[O:25])=[O:24]
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참가 물질

6

반응물 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 2773573(Oxan-4-yl)methanolHCID 66726144Ethyl 7-hydroxy-5-[4-(methylsulfonyl)phenoxy]-1H-indole-2-carboxylate

생성물 1

HCID 66898356Ethyl 5-[4-(methylsulfonyl)phenoxy]-7-(tetrahydro-2H-pyran-4-ylmethoxy)-1H-indole-2-carboxylate수율 128.8%

시약·촉매·용매

1
HCID 8028Tetrahydrofuran용매

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온도
50 °C

실험 절차

A mixture of ethyl 7-hydroxy-5-[4-(methylsulfonyl)phenoxy]-1H-indole-2-carboxylate (400 mg), tetrahydro-2H-pyran-4-ylmethanol (250 mg), 1,1′-(azodicarbonyl)dipiperidine (540 mg), tributylphosphine (0.5 mL) and tetrahydrofuran (10 mL) was stirred at 50° C. for 13 hr. The reaction solution was allowed to cool to room temperature, and the precipitated solid was filtered off. The filtrate was concentrated under reduced pressure, and the residue was subjected to basic silica gel column chromatography (ethyl acetate:hexane=3:97-45:55, volume ratio) to give the crude title compound (650 mg) as an orange oil. MS 474 (MH+).

후처리

  1. temperatureto cool to room temperature
  2. filtrationthe precipitated solid was filtered off
  3. concentrationThe filtrate was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-92b7cddafdf649508cb2c98781554c14
출처 데이터셋
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08673942B2

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