Potassium Carbonate → 3-[1-(4-Chloro-benzyl)-5-(pyridin-2-ylmethoxy)-1H-pyrrolo[3,2-b]pyridin-2-yl]-2,2-dimethyl-propionic acid ethyl ester

HRID 1713432ノート

反応式

HRID 1713432 の反応式
[CH2:1]([O:3][C:4](=[O:27])[C:5]([CH3:26])([CH3:25])[CH2:6][C:7]1[N:15]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[C:14]2[C:9](=[N:10][C:11]([OH:24])=[CH:12][CH:13]=2)[CH:8]=1)[CH3:2].Cl[CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=1.C([O-])([O-])=O.[K+].[K+]>CC(C)=O.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH2:1]([O:3][C:4](=[O:27])[C:5]([CH3:26])([CH3:25])[CH2:6][C:7]1[N:15]([CH2:16][C:17]2[CH:18]=[CH:19][C:20]([Cl:23])=[CH:21][CH:22]=2)[C:14]2[C:9](=[N:10][C:11]([O:24][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=3)=[CH:12][CH:13]=2)[CH:8]=1)[CH3:2]

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 23393Picolyl chlorideHCID 178471285HCID 178471285、化合物

生成物 1

HCID 597547723-[1-(4-Chloro-benzyl)-5-(pyridin-2-ylmethoxy)-1H-pyrrolo[3,2-b]pyridin-2-yl]-2,2-dimethyl-propionic acid ethyl ester

試薬・触媒・溶媒 3

HCID 67553Tetrabutylammonium Iodide触媒HCID 180Acetone溶媒HCID 962Water溶媒

反応条件

温度
65 °C

実験手順

3-[1-(4-Chlorobenzyl)-5-hydroxy-1H-pyrrolo[3,2-b]pyridin-2-yl]-2,2-dimethyl-propionic acid ethyl ester (0.100 g, 0.26 mmol) was dissolved in acetone (2 mL), and 2-chloromethyl-pyridine (0.064 g, 0.39 mmol), tetrabutylammonium iodide (0.095 g, 0.26 mmol) and K2CO3 (0.107 g, 0.77 mol) were added. The mixture was stirred at 65° C. overnight, and two products were observed by TLC analysis. The reaction was cooled to room temperature, diluted with water, and extracted with EtOAc three times. The combined organic layers were washed with water, brine, dried over MgSO4, filtered, and concentrated to give a 1:2 mixture of the O-alkylated and N-alkylated products. The crude material was purified by preparative TLC to obtain the O-alkylated title compound.

後処理

  1. temperatureThe reaction was cooled to room temperature
  2. extractionextracted with EtOAc three times
  3. washThe combined organic layers were washed with water, brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give
  8. additiona 1:2 mixture of the O-alkylated and N-alkylated products
  9. customThe crude material was purified by preparative TLC

出典と根拠

ORDレコード
ord-40208653b2ef48a29914d934a9518560
出典データセット
uspto-grants-2010_09
特許番号
US07795274B2

反応ノート

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