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Tributylphosphine → Ethyl 3-cyclopropyl-3-(3-(((5-(2-fluoro-5-methoxyphenyl)-6-neopentylpyridin-2-yl)oxy)methyl)phenyl)propanoate

HRID 1049411
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HRID 1049411 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:11]=[CH:12][C:13]([OH:21])=[N:14][C:15]=1[CH2:16][C:17]([CH3:20])([CH3:19])[CH3:18].[CH:22]1([CH:25]([C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([CH2:38]O)[CH:33]=2)[CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:24][CH2:23]1.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.C(P(CCCC)CCCC)CCC>C1COCC1>[CH:22]1([CH:25]([C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([CH2:38][O:21][C:13]3[CH:12]=[CH:11][C:10]([C:3]4[CH:4]=[C:5]([O:8][CH3:9])[CH:6]=[CH:7][C:2]=4[F:1])=[C:15]([CH2:16][C:17]([CH3:18])([CH3:20])[CH3:19])[N:14]=3)[CH:33]=2)[CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:24][CH2:23]1
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6

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HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 117759876Ethyl 3-cyclopropyl-3-(3-(hydroxymethyl)phenyl)propanoateHCID 178491816HCID 178491816, 화합물

생성물 1

HCID 117760107Ethyl 3-cyclopropyl-3-(3-(((5-(2-fluoro-5-methoxyphenyl)-6-neopentylpyridin-2-yl)oxy)methyl)phenyl)propanoate수율 71.3%

시약·촉매·용매

1
HCID 8028Tetrahydrofuran용매2회

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온도
0 °C

실험 절차

To a solution of 5-(2-fluoro-5-methoxyphenyl)-6-neopentylpyridin-2-ol (300 mg) in THF (20 mL) were added a solution of ethyl 3-cyclopropyl-3-(3-(hydroxymethyl)phenyl)propanoate (283 mg) in THF (5.0 mL), 1,1′-(azodicarbonyl)dipiperidine (523 mg) and tri-n-butylphosphine (420 mg) at 0° C., and the mixture was stirred at 0° C. for 5 min. The mixture was further stirred at room temperature for 16 hr, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (384 mg) as a colorless oil.

후처리

  1. stirringThe mixture was further stirred at room temperature for 16 hr
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-b6839f65e3d746e484f3fe5449341022
출처 데이터셋
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09382188B2

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