Methanesulfonic Acid → 6-Chloro-3-iodo-1-tetrahydropyran-2-yl-pyrazolo[4,3-c]pyridine

HRID 1778797노트

반응식

HRID 1778797 반응식
[Cl:1][C:2]1[N:7]=[CH:6][C:5]2[C:8]([I:11])=[N:9][NH:10][C:4]=2[CH:3]=1.CS(O)(=O)=O.[O:17]1[CH:22]=[CH:21][CH2:20][CH2:19][CH2:18]1>C(Cl)Cl.O1CCCC1>[Cl:1][C:2]1[N:7]=[CH:6][C:5]2[C:8]([I:11])=[N:9][N:10]([CH:18]3[CH2:19][CH2:20][CH2:21][CH2:22][O:17]3)[C:4]=2[CH:3]=1

참가 물질

6

반응물 3

HCID 6395Methanesulfonic AcidHCID 80803,4-dihydro-2H-pyranHCID 1784778336-chloro-3-iodo-1H-pyrazolo[4,3-c]pyridine

생성물 1

HCID 867228756-Chloro-3-iodo-1-tetrahydropyran-2-yl-pyrazolo[4,3-c]pyridine수율 99%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

At r.t. to a suspension of 6-chloro-3-iodo-1H-pyrazolo[4,3-c]pyridine (0.55 g, 2.0 mmol) in methylene chloride (6 mL) and tetrahydrofuran (3 mL) was added methanesulfonic acid (20 μL, 0.4 mmol), followed by dihydropyran (0.54 mL, 5.9 mmol) (Aldrich, Cat. #: D106208). The mixture was stirred at r.t. overnight. Then, it was stirred at 60° C. for 4 h. After cooling it was concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (0-50%) to afford the desired product (0.72 g).

후처리

  1. stirringThen, it was stirred at 60° C. for 4 h
  2. temperatureAfter cooling it
  3. concentrationwas concentrated under reduced pressure
  4. customThe residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (0-50%)

출처 및 근거

ORD 기록
ord-8c2ccc21f20845d6803919f0689c74dd
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09266892B2

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