Methyl iodide → 2-(3-Methoxy-azetidin-1-yl)-5-nitro-pyridine

HRID 2236196Notes

Reaction equation

[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH2:13][CH:12]([OH:14])[CH2:11]2)=[N:8][CH:9]=1)([O-:3])=[O:2].[H-].[Na+].[CH3:17]I>>[CH3:17][O:14][CH:12]1[CH2:11][N:10]([C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][N:8]=2)[CH2:13]1

Participants

Reactant 3

HCID 6328Methyl iodide

HCID 24758Sodium hydride

HCID 529372641-(5-Nitropyridin-2-yl)azetidin-3-ol

Product 1

HCID 593013622-(3-Methoxy-azetidin-1-yl)-5-nitro-pyridineYield 119.5%

Procedure

1-(5-Nitro-pyridin-2-yl)-azetidin-3-ol (97.5 mg, 0.5 mmol) was treated with 60% NaH in oil (40 mg, 1 mmol) and methyl iodide (125 uL, 2 mmol) as above to yield 125 mg of crude product that was used without further purification. ES-MS calcd for C9H11N3O3 (m/e) 209.21, obsd 210 (M+H).

Sources & evidence

ORD record: ord-96e1d8c49007425c97346a8d23e2b3d0
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07714126B2

Reaction notes

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