Dimethyl Sulfoxide → 1H-Pyrazolo[3,4-C]pyridine-5-carboxaldehyde

HRID 218473노트

반응식

HRID 218473 반응식
[NH:1]1[C:5]2=[CH:6][N:7]=[C:8]([CH2:10][OH:11])[CH:9]=[C:4]2[CH:3]=[N:2]1.CS(C)=O.CCN(CC)CC>C(Cl)Cl>[NH:1]1[C:5]2=[CH:6][N:7]=[C:8]([CH:10]=[O:11])[CH:9]=[C:4]2[CH:3]=[N:2]1

참가 물질

5

반응물 3

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 59763243(1H-pyrazolo[3,4-c]pyridin-5-yl)methanol

생성물 1

HCID 596944711H-Pyrazolo[3,4-C]pyridine-5-carboxaldehyde수율 21%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

1H-pyrazolo[3,4-c]pyridine-5-methanol (1.08 g, 7.27 mmol) was dissolved in DCM (120 mL) at rt, and DMSO (30 mL) and NEt3 (3.01 mL, 21.7 mmol) were added. After stirring for 10 min, SO3-pyridine (3.45 g, 13.45 mmol) was added. The mixture stirred at rt for ca. 1.5 hr, and quenched with sat. NH4Cl solution. The reaction mixture was extracted with DCM, washed with water and with brine, and dried with Na2SO4. The crude product was purified by a flash column to afford 1H-pyrazolo[3,4-c]pyridine-5-carboxaldehyde (220 mg, 21%).

후처리

  1. stirringThe mixture stirred at rt for ca. 1.5 hr
  2. customquenched with sat. NH4Cl solution
  3. extractionThe reaction mixture was extracted with DCM
  4. washwashed with water and with brine
  5. dry with materialdried with Na2SO4
  6. customThe crude product was purified by a flash column

출처 및 근거

ORD 기록
ord-aa23225b739e48c789af53168fac7857
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08198456B2

반응 노트

불러오는 중…