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

HRID 1778730Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 6-(3,5-dimethoxyphenyl)-3-iodo-1H-pyrazolo[4,3-c]pyridine (0.50 g, 1.3 mmol), dihydropyran (360 μL, 3.9 mmol), and methanesulfonic acid (17 μL, 0.26 mmol) in tetrahydrofuran (3 mL) and methylene chloride (7.5 mL) was stirred at 80° C. for 2 days. After cooling, to the mixture was added some triethylamine, and 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 (0.55 g). LCMS (M+H)+=466.0.

Workup

temperatureAfter cooling, to the mixture
concentrationconcentrated 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-60d85e2f1e8e49ceb35b6204578cb61b
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09266892B2

Reaction notes

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