3-Aminopyridine-2-carbaldehyde → HCID 67240037, compound

HRID 473435Notes

Reaction equation

[NH2:1][C:2]1[C:3]([CH:8]=O)=[N:4][CH:5]=[CH:6][CH:7]=1.[CH3:10][S:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20](=O)[CH2:21][C:22]([O:24][CH3:25])=[O:23])(=[O:13])=[O:12].O.O.O.O.O.O.O.[Cl-].[Ce+3].[Cl-].[Cl-]>CO>[CH3:10][S:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20]1[C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:8][C:3]2[C:2](=[CH:7][CH:6]=[CH:5][N:4]=2)[N:1]=1)(=[O:13])=[O:12]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 3-aminopicolinaldehyde (1.09 g, 8.97 mmol), methyl 3-(2-(methylsulfonyl)phenyl)-3-oxopropanoate (2.3 g, 8.97 mmol) and cerium chloride heptahydrate (587 mg, 1.79 mmol) was heated to 100° C. for 3 h. The residue was dissolved in MeOH and purified by column chromatography on neutral alumina using 0-50% EtOAc in hexane to give methyl 2-(2-(methylsulfonyl)phenyl)-1,5-naphthyridine-3-carboxylate (800 mg, 26% yield): 1H NMR (400 MHz, DMSO-d6) δ 3.155 (s, 3H), 3.688 (s, 3H), 7.486-7.507 (m, 1H), 7.733-7.816 (m, 2H), 7.951-7.982 (m, 1H), 8.059-8.081 (m, 1H), 8.510 (d, J=8.4 Hz, 1H), 8.965 (s, 1H), 9.165-9.178 (m, 1H); LC-MS (ESI) m/z 342.9 [M+H]+.

Workup

custompurified by column chromatography on neutral alumina using 0-50% EtOAc in hexane

Sources & evidence

ORD record: ord-9e69a8df019f4c408d22c8e7d7644c17
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08633313B2

Reaction notes

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