Methanesulfonic Acid → 6-chloro-3-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine

HRID 1778772Notes

Reaction equation

HRID 1778772 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]2[NH:8][N:9]=[C:10]([I:11])[C:5]2=[CH:4][CH:3]=1.[O:12]1[CH:17]=[CH:16][CH2:15][CH2:14][CH2:13]1.CS(O)(=O)=O>C(Cl)Cl.O1CCCC1>[Cl:1][C:2]1[N:7]=[C:6]2[N:8]([CH:13]3[CH2:14][CH2:15][CH2:16][CH2:17][O:12]3)[N:9]=[C:10]([I:11])[C:5]2=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6395Methanesulfonic AcidHCID 80803,4-dihydro-2H-pyranHCID 178477878HCID 178477878, compound

Product 1

HCID 867228676-chloro-3-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridineYield 88%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 6-chloro-3-iodo-1H-pyrazolo[3,4-b]pyridine (0.70 g, 2.5 mmol), dihydropyran (690 μL, 7.5 mmol) and methanesulfonic acid (33 μL, 0.50 mmol) in methylene chloride (30 mL) and tetrahydrofuran (10 mL) in reaction flask was stirred at r.t. overnight. 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 (0.80 g). LCMS (M-84+H)+=279.9.

Workup

  1. customin reaction flask
  2. concentrationIt was concentrated under reduced pressure
  3. customThe residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (0-50%)

Sources & evidence

ORD record
ord-8183e5d87ed34f47887e223f9904c23b
Source dataset
uspto-grants-2016_02
Patent number
US09266892B2

Reaction notes

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