Stannous chloride dihydrate → 5-((2-Chloropyridin-4-yl)oxy)-6-methylpyridin-2-amine

HRID 1049240Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[C:10]([CH3:18])=[N:11][C:12]([N+:15]([O-])=O)=[CH:13][CH:14]=2)[CH:5]=[CH:4][N:3]=1.O.O.[Sn](Cl)Cl.C([O-])(O)=O.[Na+]>CCO>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[N:11][C:10]=2[CH3:18])[CH:5]=[CH:4][N:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of Example A4 (1 g, 3.76 mmol) in EtOH (37.6 mL) was treated with tin(II) chloride dihydrate (4.25 g, 18.82 mmol) and stirred at 80° C. for 30 h. The mixture was cooled to RT, treated slowly with satd. NaHCO3 (5 mL), stirred for several minutes and filtered through diatomaceous earth. The filtrate was dried over Na2SO4 and concentrated to dryness to afford crude 5-((2-chloropyridin-4-yl)oxy)-6-methylpyridin-2-amine (645 mg, 73%) as an orange solid which was used without further purification. MS (ESI) m/z: 236.1 (M+H+).

Workup

temperatureThe mixture was cooled to RT
additiontreated slowly with satd
filtrationfiltered through diatomaceous earth
dry with materialThe filtrate was dried over Na2SO4
concentrationconcentrated to dryness

Sources & evidence

ORD record: ord-cabf1012490a44c99473fb5a30641051
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09382228B2

Reaction notes

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