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

HRID 1778797Notes

Reaction equation

HRID 1778797 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  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%)

Sources & evidence

ORD record
ord-8c2ccc21f20845d6803919f0689c74dd
Source dataset
uspto-grants-2016_02
Patent number
US09266892B2

Reaction notes

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