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

HRID 250576ノート

反応式

HRID 250576 の反応式
[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]

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

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.

後処理

  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%)

出典と根拠

ORDレコード
ord-9eb2dedc06914847ab29157300811bfd
出典データセット
uspto-grants-2011_01
特許番号
US07863288B2

反応ノート

読み込み中…