Acetic Acid → 5-Fluoro-2-(3-fluoro-4-((E)-2-nitro-vinyl)phenoxymethyl)-pyridine

HRID 640362

Reaction equation

C(O)(=O)C.[F:5][C:6]1[CH:13]=[C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][N:17]=2)[CH:11]=[CH:10][C:7]=1[CH:8]=O.[N+:23]([CH3:26])([O-:25])=[O:24].C([O-])(=O)C.[NH4+]>C(OCC)(=O)C.O>[F:22][C:19]1[CH:20]=[CH:21][C:16]([CH2:15][O:14][C:12]2[CH:11]=[CH:10][C:7](/[CH:8]=[CH:26]/[N+:23]([O-:25])=[O:24])=[C:6]([F:5])[CH:13]=2)=[N:17][CH:18]=1

Participants

Conditions

Temperature: 110 °C

Procedure

To an acetic acid (20.0 mL) solution of 2-fluoro-4-(5-fluoro-pyridin-2-ylmethoxy)-benzaldehyde (901 mg, 3.62 mmol) described in Manufacturing Example 96-1-1 were added nitromethane (1.10 g, 18.1 mmol) and ammonium acetate (558 mg, 7.24 mmol) under nitrogen atmosphere, which was stirred for 2 hours at 110° C. Water and ethyl acetate were added to the reaction mixture, and the organic layer was extracted with ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure to obtain the title compound (1.00 g) as a crude product.

Workup

extractionthe organic layer was extracted with ethyl acetate
washThe organic layer was washed with water and saturated aqueous sodium chloride
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
concentrationThe filtrate was concentrated under a reduced pressure

Sources & evidence

ORD record: ord-704e668282074e309d700a70e2b2d372
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07691882B2

Linked notes

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