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

HRID 2278893Notes

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 A6 (1 g, 3.76 mmol) in EtOH (38 mL) was treated with tin(II) chloride dihydrate (4.25 g, 18.8 mmol), heated at 80° C. for 30 h, then cooled to RT and treated slowly with satd. NaHCO3. The mixture was stirred for several minutes, the solids removed via filtration through diatomaceous earth and 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%) which was used without further purification. MS (ESI) m/z: 236.1 (M+H+).

Workup

temperaturecooled to RT
additiontreated slowly with satd
customthe solids removed via filtration through diatomaceous earth
dry with materialthe filtrate was dried over Na2SO4
concentrationconcentrated to dryness

Sources & evidence

ORD record: ord-2125390650f44b3f85985cc64df83f14
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133183B2

Reaction notes

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