Sodium hydride → 2,2-Dimethyl-propionic acid 5-bromo-3-(2-methoxy-phenyl)-pyrazolo[3,4,b]pyridine-1-ylmethyl ester

HRID 886615노트

반응식

HRID 886615 반응식
[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[O:17][CH3:18])=[N:9][NH:8][C:5]2=[N:6][CH:7]=1.[H-].[Na+].Cl[CH2:22][O:23][C:24](=[O:29])[C:25]([CH3:28])([CH3:27])[CH3:26]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[O:17][CH3:18])=[N:9][N:8]([CH2:22][O:23][C:24](=[O:29])[C:25]([CH3:28])([CH3:27])[CH3:26])[C:5]2=[N:6][CH:7]=1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 87885Chloromethyl pivalateHCID 178489372HCID 178489372, 화합물

생성물 1

HCID 579758192,2-Dimethyl-propionic acid 5-bromo-3-(2-methoxy-phenyl)-pyrazolo[3,4,b]pyridine-1-ylmethyl ester수율 62%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

반응 조건

온도
-40 °C

실험 절차

To a solution of 5-bromo-3-(2-methoxy-phenyl)-1H-pyrazolo[3,4-b]pyridine (4.8 g, 15.8 mmol) in DMF (60 ml) at −40° C. under nitrogen, sodium hydride (1.1 g, 47.3 mmol) was added. The mixture was stirred at −40° C. for 1 hour. Then 2,2-dimethyl-propionic acid chloromethyl ester (6.9 ml, 47.3 mmol; chloromethyl pivalate) in DMF (20 ml) was added dropwise and the resulting mixture was allowed to stir at 40° C. for another 2 hours. The reaction was quenched with saturated aqueous NH4Cl (40 ml) and worked up with ethyl acetate, brine, dried with Na2SO4 and evaporated. Silica gel chromatography of the crude using a gradient of ethyl acetate and hexane afforded 2,2-dimethyl-propionic acid 5-bromo-3-(2-methoxy-phenyl)-pyrazolo[3,4,b]pyridine-1-ylmethyl ester (4.1 g, 62% yield). 1H NMR (500 MHz, DMSO-d6) δ 1.11 (s, 9H), 3.85 (s, 3H), 6.46 (s, 2H), 7.09 (m, 1H), 7.24 (d, 1H), 7.51 (m, 1H), 7.60 (d, 1H), 8.43 (s, 1H), 8.74 (s, 1H).

후처리

  1. stirringto stir at 40° C. for another 2 hours
  2. customThe reaction was quenched with saturated aqueous NH4Cl (40 ml)
  3. dry with materialdried with Na2SO4
  4. customevaporated

출처 및 근거

ORD 기록
ord-a1a9e3e0a0504ab6977b464bc00c22f3
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08242280B2

반응 노트

불러오는 중…