Water → 5-Chloro-6-iodopyridine-2,3-diamine

Temperature

70 °C

To a suspension of 5-chloro-6-iodo-3-nitropyridin-2-amine (18.9 g, 63.1 mmol) in EtOH (100 mL) was added tin (II) chloride dihydrate (57 g, 252 mmol). The mixture was heated at 70° C. for 0.5 h. The r×n was warmed to rt and treated with a slurry of 150 mL water and 60 g KF and stirred for 0.5 h. The mixture was then partitioned between ethyl acetate (300 mL) and water (300 mL). The ethyl acetate layer was washed with brine, dried over magnesium sulfate and filtered through a 100 g pad of silica gel. The filtrate was concentrated and dried under vacuum to give an off-white solid, which was used in next step without further purification. LC-MS: calculated for C5H5ClIN3 269.47, observed m/e: 269.99 (M+H)+ (Rt 1.35/5 min)

1. temperatureThe r×n was warmed to rt
2. customThe mixture was then partitioned between ethyl acetate (300 mL) and water (300 mL)
3. washThe ethyl acetate layer was washed with brine
4. dry with materialdried over magnesium sulfate
5. filtrationfiltered through a 100 g pad of silica gel
6. concentrationThe filtrate was concentrated
7. customdried under vacuum
8. customto give an off-white solid, which
9. customwas used in next step without further purification
10. custom269.99 (M+H)+ (Rt 1.35/5 min)

ORD record

ord-af8d60c39e8d4e929f259279ded07854

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09290517B2