Methanesulfonic Acid → 6-(3,5-dimethoxyphenyl)-3-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[4,3-b]pyridine

HRID 1778768Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[CH:12]=[C:13]3[NH:19][N:18]=[C:17]([I:20])[C:14]3=[N:15][CH:16]=2)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.[O:21]1[CH:26]=[CH:25][CH2:24][CH2:23][CH2:22]1.CS(O)(=O)=O>C(Cl)Cl.O1CCCC1>[CH3:10][O:9][C:7]1[CH:6]=[C:5]([C:11]2[CH:12]=[C:13]3[N:19]([CH:22]4[CH2:23][CH2:24][CH2:25][CH2:26][O:21]4)[N:18]=[C:17]([I:20])[C:14]3=[N:15][CH:16]=2)[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 6-(3,5-dimethoxyphenyl)-3-iodo-1H-pyrazolo[4,3-b]pyridine (0.54 g, 1.4 μmmol), dihydropyran (0.39 mL, 4.2 mmol) and methanesulfonic acid (18 μL, 0.28 mmol) in methylene chloride (6 mL) and tetrahydrofuran (2 mL) in a sealed reaction vial was stirred at 50° C. for 3 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 (0.60 g). LCMS (M+H)+=465.9.

Workup

customin a sealed reaction vial
temperatureAfter cooling it
concentrationwas concentrated under reduced pressure
customThe residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (0-50%)

Sources & evidence

ORD record: ord-ebadb42ed2854cfebdcbf7f1ab9ac829
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09266892B2

Reaction notes

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