Potassium Carbonate → N-(4-(cyclopropyl(6-methoxypyridin-3-yl)methoxy)-3-methoxybenzyl)-5-iodo-3-nitropyridin-2-amine

HRID 706501Notes

Reaction equation

[CH:1]1([CH:4]([C:16]2[CH:17]=[N:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=2)[O:5][C:6]2[CH:11]=[CH:10][C:9]([CH2:12][NH2:13])=[CH:8][C:7]=2[O:14][CH3:15])[CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].Cl[C:31]1[C:36]([N+:37]([O-:39])=[O:38])=[CH:35][C:34]([I:40])=[CH:33][N:32]=1>C(#N)C>[CH:1]1([CH:4]([C:16]2[CH:17]=[N:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=2)[O:5][C:6]2[CH:11]=[CH:10][C:9]([CH2:12][NH:13][C:31]3[C:36]([N+:37]([O-:39])=[O:38])=[CH:35][C:34]([I:40])=[CH:33][N:32]=3)=[CH:8][C:7]=2[O:14][CH3:15])[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a stirred solution of (4-(cyclopropyl(6-methoxypyridin-3-yl)methoxy)-3-methoxyphenyl)methanamine (2.50 g, 7.95 mmol) and potassium carbonate (1.41 g, 10.20 mmol) in acetonitrile (10 mL) was added 2-chloro-5-iodo-3-nitropyridine (2.90 g, 10.20 mmol). The resulting mixture was heated to 80° C. After 2 h, the mixture was filtered, and the filtrate was concentrated. Chromatographic purification of the residue (silica gel, 20% ethyl acetate in petroleum ether elute) afforded 2.60 g (58%) of N-(4-(cyclopropyl(6-methoxypyridin-3-yl)methoxy)-3-methoxybenzyl)-5-iodo-3-nitropyridin-2-amine as a yellow oil.

Workup

filtrationthe mixture was filtered
concentrationthe filtrate was concentrated
customChromatographic purification of the residue (silica gel, 20% ethyl acetate in petroleum ether elute)

Sources & evidence

ORD record: ord-c21ddea1c366453eade9cbb9fb2d3674
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09174986B2

Reaction notes

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