Stannous chloride dihydrate → 5-Bromo-N2-methylpyridine-2,3-diamine

Temperature

70 °C

A suspension of (5-bromo-3-nitro-pyridin-2-yl)-methyl-amine (Stage 67.1.5, 4.58 g, 19.75 mmol) and tin dichloride dihydrate (Acros, Basel, Switzerland, 13.38 g, 59.3 mmol) in 200 ml of THF was heated at 70° C. for 220 min. The solvent was removed by evaporation and the residue taken in CH2Cl2 (100 ml) and 5 M aqueous NaOH (50 ml) and stirred until all the solid was dissolved. The organic layer was separated and the aqueous layer was extracted with CH2Cl2. The combined organic layers were washed with brine, dried over Na2SO4, filtered and evaporated to give the title compound as a brown solid. (HPLC: tR 1.69 min (Method A); M+H=202, 204 MS-ES).

1. customThe solvent was removed by evaporation
2. dissolutionwas dissolved
3. customThe organic layer was separated
4. extractionthe aqueous layer was extracted with CH2Cl2
5. washThe combined organic layers were washed with brine
6. dry with materialdried over Na2SO4
7. filtrationfiltered
8. customevaporated

ORD record

ord-8ecbd0768a1849deae16685051c57af1

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08476294B2