Water → HCID 90403195, compound

HRID 718185Notes

Reaction equation

Br[C:2]1[C:3]([CH3:12])=[N:4][C:5]([N+:9]([O-:11])=[O:10])=[CH:6][C:7]=1[CH3:8].[Cl:13][C:14]1[CH:19]=[C:18]([OH:20])[CH:17]=[CH:16][N:15]=1.C([O-])([O-])=O.[K+].[K+].O>CC(N(C)C)=O>[Cl:13][C:14]1[CH:19]=[C:18]([O:20][C:2]2[C:3]([CH3:12])=[N:4][C:5]([N+:9]([O-:11])=[O:10])=[CH:6][C:7]=2[CH3:8])[CH:17]=[CH:16][N:15]=1

Participants

Conditions

Temperature: 100 °C

Procedure

3-Bromo-2,4-dimethyl-6-nitropyridine (2.2 g, 9.5 mmol) and 2-chloro-4-hydroxypyridine (2.5 g, 19 mmol) were combined in DMA (10 mL) and the solution was sonicated and sparged with Ar for 10 min. K2CO3 (4.0 g, 29 mmol) was added and the reaction mixture was stirred at 100° C. for 12 h. The reaction mixture was poured into water (200 mL) and the precipitated solids were isolated by filtration. The solids were washed with ½ sat. K2CO3 (aq) (3×50 mL) and water (3×50 mL) and dried under high vacuum for 5 h. The crude product was purified by silica gel chromatography (EtOAc/hexanes) to afford 3-((2-chloropyridin-4-yl)oxy)-2,4-dimethyl-6-nitropyridine (0.50 g, 19%) as a brown solid. 1H NMR (400 MHz, DMSO-d6): δ 8.33-8.30 (m, 2H), 7.15 (d, J=2.3 Hz, 1H), 7.01 (dd, J=5.8, 2.3 Hz, 1H), 2.33 (s, 3H), 2.23 (s, 3H); MS (ESI) m/z: 280.0 (M+H+).

Workup

customthe solution was sonicated
customsparged with Ar for 10 min
customthe precipitated solids were isolated by filtration
washThe solids were washed with ½ sat. K2CO3 (aq) (3×50 mL) and water (3×50 mL)
customdried under high vacuum for 5 h
customThe crude product was purified by silica gel chromatography (EtOAc/hexanes)

Sources & evidence

ORD record: ord-551d8bed0bb74dcbad373c5ab2a51701
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193719B2

Reaction notes

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