Pyridine → 3-bromo-1-(tert-butyldimethylsilyl)-5-(3-fluorophenyl)-1H-pyrrolo[2,3-b]pyridine

HRID 493150ノート

反応式

HRID 493150 の反応式
[Br:1]Br.[C:3]([Si:7]([CH3:25])([CH3:24])[N:8]1[C:12]2=[N:13][CH:14]=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[CH:18]=3)[CH:16]=[C:11]2[CH:10]=[CH:9]1)([CH3:6])([CH3:5])[CH3:4].N1C=CC=CC=1.C([O-])(O)=O.[Na+].[O-]S([O-])(=S)=O.[Na+].[Na+]>C(Cl)(Cl)(Cl)Cl.C(Cl)(Cl)Cl>[Br:1][C:10]1[C:11]2[C:12](=[N:13][CH:14]=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[CH:18]=3)[CH:16]=2)[N:8]([Si:7]([C:3]([CH3:6])([CH3:5])[CH3:4])([CH3:25])[CH3:24])[CH:9]=1

参加物

7

反応物 4

HCID 1049PyridineHCID 24408BromineHCID 22607107sodium thiosulfate NaHCO3HCID 497590641-(tert-Butyl-dimethyl-silanyl)-5-(3-fluoro-phenyl)-1H-pyrrolo[2,3-b]pyridine

生成物 1

HCID 576811263-bromo-1-(tert-butyldimethylsilyl)-5-(3-fluorophenyl)-1H-pyrrolo[2,3-b]pyridine収率 95.8%

試薬・触媒・溶媒 2

HCID 5943Carbon Tetrachloride溶媒HCID 6212Chloroform溶媒

実験手順

A solution of Br2 (1.12 mL, 21.8 mmol) in CCl4 was added dropwise to a stirred and cooled (0° C.) solution of 8 (7.10 g, 21.8 mmol) and pyridine (2.1 mL, 26.2 mmol) in dry CHCl3 (330 mL). Progress of the reaction was followed by TLC. When the reaction was completed, aqueous NaHCO3—Na2S2O3 solution was added. The organic solution was separated and the aqueous layer was extracted with CH2Cl2 (3×100 mL). Combined organic solutions were dried (MgSO4), concentrated and purified by SGC with hexane:benzene as eluent in gradient (up to 14% benzene) to afford 9 (8.47 g, 91%) as tan solid. 1H NMR (400 MHz, CDCl3) δ 0.65 (s, 6H), 0.97 (s, 9H), 7.02-7.10 (m, 1H), 7.29 (s, 1H), 7.33-7.38 (m, 1H), 7.40-7.47 (m, 2H), 7.97 (d, J=2.2 Hz, 1H), 8.51 (d, J=2.2 Hz, 1H).

後処理

  1. customThe organic solution was separated
  2. extractionthe aqueous layer was extracted with CH2Cl2 (3×100 mL)
  3. dry with materialCombined organic solutions were dried (MgSO4)
  4. concentrationconcentrated
  5. custompurified by SGC with hexane

出典と根拠

ORDレコード
ord-07c2f4b6f0f24ecebe908cbb5e1749b3
出典データセット
uspto-grants-2009_05
特許番号
US07534800B2

反応ノート

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