Stannous Chloride → HCID 58683947, compound

HRID 1897989Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([N+:16]([O-])=O)[C:5]([C:8]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)=[O:9])=[N:6][CH:7]=1.Cl[Sn]Cl>CCO>[NH2:16][C:4]1[C:5]([C:8]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)=[O:9])=[N:6][CH:7]=[C:2]([Cl:1])[CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of the (5-Chloro-3-nitro-pyridin-2-yl)-pyridin-3-yl-methanone from Step 2 above (30 mg, 0.11 mmol) and SnCl2 (200 mg, 0.88 mmol) in EtOH (3 mL) was heated at 80° C. in an oil bath for 3 days. The progress of the reaction was followed by LCMS and upon completion the solvent was removed and treated with aqueous NaOH to adjust the pH to 10-11. This cloudy mixture was extracted with EtOAc and washed with water and brine. The combined extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure and the residue separated by preparative HPLC (20→80% gradient of ACN-water) and pure product fractions were treated with NaHCO3 and extracted with EtOAc to provide (3-amino-5-chloro-pyridin-2-yl)-pyridin-3-yl-methanone. MS m/z: 234.1 (M+H).

Workup

customwas removed
additiontreated with aqueous NaOH
extractionThis cloudy mixture was extracted with EtOAc
washwashed with water and brine
dry with materialThe combined extracts were dried over anhydrous Na2SO4
filtrationfiltered
concentrationconcentrated under reduced pressure
customthe residue separated by preparative HPLC (20→80% gradient of ACN-water) and pure product fractions
additionwere treated with NaHCO3
extractionextracted with EtOAc

Sources & evidence

ORD record: ord-f4f45cc8b4fb451eab36d85538f21015
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08519135B2

Reaction notes

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