Water → N-{2,4-difluoro-3-[hydroxy-(1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-methyl]-phenyl}-3-methoxy-benzenesulfonamide

HRID 250576

반응식

HRID 250576 반응식
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][S:10]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=1)(=[O:12])=[O:11].C([N-]C(C)C)(C)C.[Li+].[CH:29]([Si:32]([CH:47]([CH3:49])[CH3:48])([CH:44]([CH3:46])[CH3:45])[N:33]1[C:37]2=[N:38][CH:39]=[CH:40][CH:41]=[C:36]2[C:35]([CH:42]=[O:43])=[CH:34]1)([CH3:31])[CH3:30].O>O1CCCC1>[F:1][C:2]1[C:7]([CH:42]([OH:43])[C:35]2[C:36]3[C:37](=[N:38][CH:39]=[CH:40][CH:41]=3)[N:33]([Si:32]([CH:44]([CH3:46])[CH3:45])([CH:47]([CH3:49])[CH3:48])[CH:29]([CH3:30])[CH3:31])[CH:34]=2)=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][S:10]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=1)(=[O:11])=[O:12]

참가 물질

6

반응물 4

HCID 962WaterHCID 2724682Lithium diisopropylamideHCID 497589651H-Pyrrolo[2,3-B]pyridine-3-carboxaldehyde, 1-[tris(1-methylethyl)silyl]-HCID 58086624N-(2,4-difluorophenyl)-3-methoxybenzenesulfonamide

생성물 1

HCID 58182210N-{2,4-difluoro-3-[hydroxy-(1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-methyl]-phenyl}-3-methoxy-benzenesulfonamide

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-78 °C

실험 절차

To N-(2,4-difluoro-phenyl)-3-methoxy-benzenesulfonamide (91, 0.148 g, 0.494 mmol) in tetrahydrofuran (10.0 mL) cooled in a −78° C. acetone/dry ice bath, under an atmosphere of nitrogen, was added lithium diisopropylamide (0.85 M in tetrahydrofuran, 1.45 mL, 1.23 mmol) dropwise. After 30 minutes, 1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde (96, 0.15 g, 0.500 mmol, prepared as described in Example 12) was added in tetrahydrofuran (2.0 mL) into the reaction dropwise. Then the reaction was stirred for 1 hour at −78° C. and allowed to reach room temperature. The reaction was poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with 40% ethyl acetate in hexane to give light yellow solid (92, 0.080 g, 26.8%). MS (ES1)[M+H+]+=602.

후처리

  1. customto reach room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. custompurified by silica gel column chromatography
  8. washeluting with 40% ethyl acetate in hexane
  9. customto give light yellow solid (92, 0.080 g, 26.8%)

출처 및 근거

ORD 기록
ord-9eb2dedc06914847ab29157300811bfd
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07863288B2

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