Hydrochloric Acid → 2-(1,2-Dihydroxy-1-methyl-ethyl)-6-trifluoromethyl-1H-indole-5-carbonitrile

HRID 646584

반응식

HRID 646584 반응식
C([Si](C)(C)[O:6][CH2:7][C:8]([C:11]1[N:12](S(C)(=O)=O)[C:13]2[C:18]([CH:19]=1)=[CH:17][C:16]([C:20]#[N:21])=[C:15]([C:22]([F:25])([F:24])[F:23])[CH:14]=2)([OH:10])[CH3:9])(C)(C)C.[OH-].[Na+].Cl>CO.O>[OH:10][C:8]([C:11]1[NH:12][C:13]2[C:18]([CH:19]=1)=[CH:17][C:16]([C:20]#[N:21])=[C:15]([C:22]([F:25])([F:23])[F:24])[CH:14]=2)([CH3:9])[CH2:7][OH:6]

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 668647662-[2-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-1-methyl-ethyl]-1-methanesulfonyl-6-trifluoromethyl-1H-indole-5-carbonitrile

생성물 1

HCID 668644952-(1,2-Dihydroxy-1-methyl-ethyl)-6-trifluoromethyl-1H-indole-5-carbonitrile

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

반응 조건

온도
50 °C

실험 절차

To a suspension of 2-[2-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-1-methyl-ethyl]-1-methanesulfonyl-6-trifluoromethyl-1H-indole-5-carbonitrile (9.22 g, 0.01935 mole) in methanol (150 mL), a solution of NaOH (4.64 g 0.1161 mole) in water (25 mL) was added. The resulting mixture was heated in an oil-bath at 50° C. for 4 hr and then stirred at room temperature overnight. To the reaction mixture was then added 1N HCl until the pH was 3. The aqueous mixture was extracted with EtOAc, the organic layer was washed with water, brine, then dried over MgSO4. The solvent was stripped off, the residue was triturated with DCM, and the resulting solid collected by filtration to yield the title compound as a light grey solid.

후처리

  1. extractionThe aqueous mixture was extracted with EtOAc
  2. washthe organic layer was washed with water, brine
  3. dry with materialdried over MgSO4
  4. customthe residue was triturated with DCM
  5. filtrationthe resulting solid collected by filtration

출처 및 근거

ORD 기록
ord-9b7ba8d2ac5f47c08f9ee587fe5720fd
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07705147B2

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