Sodium Carbonate → ethyl 5-chloro-1-isopropyl-6-(2,2,6,6-tetramethyl-1,2,3,6-tetrahydro pyridin-4-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylate

HRID 1501590노트

반응식

HRID 1501590 반응식
[Cl:1][C:2]1[C:7](OS(C(F)(F)F)(=O)=O)=[N:6][C:5]2[N:16]([CH:19]([CH3:21])[CH3:20])[N:17]=[CH:18][C:4]=2[C:3]=1[C:22]([O:24][CH2:25][CH3:26])=[O:23].[CH3:27][C:28]1([CH3:45])[CH2:33][C:32](B2OC(C)(C)C(C)(C)O2)=[CH:31][C:30]([CH3:44])([CH3:43])[NH:29]1.C([O-])([O-])=O.[Na+].[Na+].CO.C(Cl)Cl>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:1][C:2]1[C:7]([C:32]2[CH2:31][C:30]([CH3:44])([CH3:43])[NH:29][C:28]([CH3:45])([CH3:27])[CH:33]=2)=[N:6][C:5]2[N:16]([CH:19]([CH3:21])[CH3:20])[N:17]=[CH:18][C:4]=2[C:3]=1[C:22]([O:24][CH2:25][CH3:26])=[O:23]

참가 물질

7

반응물 4

HCID 10340Sodium CarbonateHCID 21226129Dichloromethane methanolHCID 467380232,2,6,6-Tetramethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridineHCID 86703417ethyl 5-chloro-1-isopropyl-6-(((trifluoromethyl)sulfonyl)oxy)-1H-pyrazolo[3,4-b]pyridine-4-carboxylate

생성물 1

HCID 68351064ethyl 5-chloro-1-isopropyl-6-(2,2,6,6-tetramethyl-1,2,3,6-tetrahydro pyridin-4-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylate수율 46.2%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 312751,4-Dioxane용매

반응 조건

온도
100 °C

실험 절차

A solution of ethyl 5-chloro-1-isopropyl-6-(((trifluoromethyl)sulfonyl)oxy)-1H-pyrazolo[3,4-b]pyridine-4-carboxylate (0.2 g, 0.481 mmol), 2,2,6,6-tetramethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine (0.127 g, 0.481 mmol) and Pd(PPh3)4 (0.027 g, 0.024 mmol) in 1,4-dioxane (3 mL) was purged with argon for 10 min. Then, 2M Na2CO3 solution (0.183 g, 1.734 mmol) was added to it and again argon was purged through it for 10 min. The reaction mixture was stirred at 100° C. for 1 h. After completion of the reaction, water was added to it and extraction was carried out using 10% MeOH/DCM. The combined organic layers were washed with water, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to afford crude material which was purified by column chromatography to give the desired compound (0.09 g, 45.6%).

후처리

  1. customwas purged through it for 10 min
  2. customAfter completion of the reaction, water
  3. additionwas added to it and extraction
  4. washThe combined organic layers were washed with water
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto afford crude material which
  9. customwas purified by column chromatography

출처 및 근거

ORD 기록
ord-271669b997424acb94cf6654ea2b9326
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09206157B2

반응 노트

불러오는 중…