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 1713432노트

반응식

HRID 1713432 반응식
[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]

참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 23393Picolyl chlorideHCID 178471285HCID 178471285, 화합물

생성물 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

시약·촉매·용매 3

HCID 67553Tetrabutylammonium Iodide촉매HCID 180Acetone용매HCID 962Water용매

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온도
65 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-40208653b2ef48a29914d934a9518560
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07795274B2

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