Pyridine → 3-Bromo-1-(tert-butyl-dimethyl-silanyl)-5-pyridin-3-yl-1h-pyrrolo[2,3-b]pyridine

HRID 1886818ノート

反応式

HRID 1886818 の反応式
[Br:1]Br.[C:3]([Si:7]([CH3:24])([CH3:23])[N:8]1[C:12]2=[N:13][CH:14]=[C:15]([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=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+].S([O-])([O-])(=O)=S.[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:18]=[N:19][CH:20]=[CH:21][CH:22]=3)[CH:16]=2)[N:8]([Si:7]([C:3]([CH3:6])([CH3:5])[CH3:4])([CH3:24])[CH3:23])[CH:9]=1

参加物

7

反応物 4

HCID 1049PyridineHCID 24408BromineHCID 22607107sodium thiosulfate NaHCO3HCID 575980361-(tert-Butyl-dimethyl-silanyl)-5-pyridin-3-yl-1H-pyrrolo[2,3-b]pyridine

生成物 1

HCID 575980783-Bromo-1-(tert-butyl-dimethyl-silanyl)-5-pyridin-3-yl-1h-pyrrolo[2,3-b]pyridine収率 78%

試薬・触媒・溶媒 2

HCID 5943Carbon Tetrachloride溶媒HCID 6212Chloroform溶媒

反応条件

温度
0 °C

実験手順

A solution of bromine (0.166 mL, 0.0032 mol) in 1 mL of CCl4 was added dropwise to a stirred solution of 20 (1.0 g, 0.0032 mol) and pyridine (0.314 mL, 0.0039 mol) in dry CHCl3 (30 mL) at 0° C. The reaction mixture was stirred at 0° C. for 1 h and then neutralized with 10 mL of a mixture of sodium bicarbonate-sodium thiosulfate (1:1). The organic layer was separated and further extracted with dichloromethane (3×10 mL) and the combined organics dried and concentrated in vacuo. The residue was subjected to flash chromatography (30% EtOAc-70% hexanes) to give 0.97 g (78%) of the desired material 21. 1H NMR CDCl3 8.9 (s, 1H), 8.55 (d, 1H), 8.4 (d, 1H), 8.0 (d, 1H), 7.9 (d, 1H), 7.4 (dd, 1H), 7.2 (s, 1H), 0.9 (s, 9H), 0.5 (s, 6H).

後処理

  1. customThe organic layer was separated
  2. extractionfurther extracted with dichloromethane (3×10 mL)
  3. customthe combined organics dried
  4. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-d2153a386fae470e97a263baac10518f
出典データセット
uspto-grants-2013_08
特許番号
US08501446B2

反応ノート

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