Methanol → 2-[2-(7-Ethoxy-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indol-2-yl)-4,5-dihydro-1,3-thiazol-5-yl]ethanol

HRID 1189044노트

반응식

HRID 1189044 반응식
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([O:24][C:25]2[CH:26]=[N:27][C:28]([S:31]([CH3:34])(=[O:33])=[O:32])=[CH:29][CH:30]=2)[CH:7]=[C:8]2[C:12]=1[NH:11][C:10]([C:13]1[S:14][CH:15]([CH2:18][C:19](OCC)=[O:20])[CH2:16][N:17]=1)=[CH:9]2)[CH3:2].CO.[BH4-].[Li+]>O1CCCC1>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([O:24][C:25]2[CH:26]=[N:27][C:28]([S:31]([CH3:34])(=[O:32])=[O:33])=[CH:29][CH:30]=2)[CH:7]=[C:8]2[C:12]=1[NH:11][C:10]([C:13]1[S:14][CH:15]([CH2:18][CH2:19][OH:20])[CH2:16][N:17]=1)=[CH:9]2)[CH3:2]

참가 물질

5

반응물 3

HCID 887MethanolHCID 4148881Lithium borohydride2회HCID 58237074Ethyl [2-(7-ethoxy-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indol-2-yl)-4,5-dihydro-1,3-thiazol-5-yl]acetate

생성물 1

HCID 582371202-[2-(7-Ethoxy-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indol-2-yl)-4,5-dihydro-1,3-thiazol-5-yl]ethanol수율 54%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To an ice-cooled and stirred solution of ethyl [2-(7-ethoxy-5-{[6-(methylsulfonyl)pyridin-3-yl]oxy}-1H-indol-2-yl)-4,5-dihydro-1,3-thiazol-5-yl]acetate (110 mg) in tetrahydrofuran (8 mL)-methanol (2 mL) was added lithium borohydride (25 mg), and the mixture was stirred at room temperature for 4 h, followed by an addition of lithium borohydride (25 mg). After stirring at room temperature for 3 h, the reaction mixture was partitioned between ethyl acetate and aqueous citric acid solution. The organic layer was washed with brine, dried (MgSO4), filtered, and concentrated. The residue was purified by silica gel chromatography (ethyl acetate:hexane=50:50 to 100:0, volume ratio) to give a colorless oil, which was crystallized from ethyl acetate-hexane to give the title compound (54 mg, 54%) as colorless crystals. MS 462 (MH+). mp 147-148° C.

후처리

  1. stirringAfter stirring at room temperature for 3 h
  2. customthe reaction mixture was partitioned between ethyl acetate and aqueous citric acid solution
  3. washThe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography (ethyl acetate:hexane=50:50 to 100:0, volume ratio)
  8. customto give a colorless oil, which
  9. customwas crystallized from ethyl acetate-hexane

출처 및 근거

ORD 기록
ord-b158acef402840558c49bfc9bb9f9e9a
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08673942B2

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