Aluminium lithium hydride → 3-(5-Formylpyridin-2-yl)-2-hydroxy-1H-indole-5-carbonitrile

HRID 1881331노트

반응식

HRID 1881331 반응식
[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([OH:12])=[C:6]2[C:13]1[CH:24]=[CH:23][C:16]([C:17](N(OC)C)=[O:18])=[CH:15][N:14]=1)#[N:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1.C(OCC)(=O)C>[CH:17]([C:16]1[CH:23]=[CH:24][C:13]([C:6]2[C:5]3[C:9](=[CH:10][CH:11]=[C:3]([C:1]#[N:2])[CH:4]=3)[NH:8][C:7]=2[OH:12])=[N:14][CH:15]=1)=[O:18]

참가 물질

5

반응물 2

HCID 21226445Aluminium lithium hydrideHCID 1362398576-(5-Cyano-2-hydroxy-1H-indol-3-yl)-N-methoxy-N-methylnicotinamide

생성물 1

HCID 1362769533-(5-Formylpyridin-2-yl)-2-hydroxy-1H-indole-5-carbonitrile수율 68%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To an icecold suspension of 50 mg (0.16 mmol) of 6-(5-cyano-2-hydroxy-1H-indol-3-yl)-N-methoxy-N-methylnicotin-amide from example 1.2 in THF (4 mL) were added 19.4 mg (0.51 mmol) of LiAlH4 as a solid in small portions. The resulting mixture was stirred at that temperature for further 30 min. After diluting with ethyl acetate the reaction was quenched by adding 4.2 mL of a 0.35 M solution of KHSO4. The resulting solution was stirred for further 60 min, the phases were separated, and the precipitate in the organic layer was collected by filtration, washed with water and ethyl acetate, and dried in a vacuum oven yielding a red solid. Amount 28 mg. Yield 68%.

후처리

  1. customwas quenched
  2. additionby adding 4.2 mL of a 0.35 M solution of KHSO4
  3. stirringThe resulting solution was stirred for further 60 min
  4. customthe phases were separated
  5. filtrationthe precipitate in the organic layer was collected by filtration
  6. washwashed with water and ethyl acetate
  7. customdried in a vacuum oven
  8. customyielding a red solid

출처 및 근거

ORD 기록
ord-2d0a549c23724f919c7253341a43d834
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08318793B2

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