Ammonia → N2-methyl-5-trifluoromethylsulfanylpyridine-2,3-diamine

HRID 1750053Notes

Reaction equation

Br[C:2]1[C:3]([NH:13][CH3:14])=[N:4][CH:5]=[C:6]([S:8][C:9]([F:12])([F:11])[F:10])[CH:7]=1.C(CC(=O)C)(=O)C.C(=O)([O-])[O-].[Cs+].[Cs+].[NH3:28]>[Cu+2].C(CC(=O)C)(=O)C.O.CN1C(=O)CCC1>[CH3:14][NH:13][C:3]1[C:2]([NH2:28])=[CH:7][C:6]([S:8][C:9]([F:12])([F:11])[F:10])=[CH:5][N:4]=1

Participants

Conditions

Temperature: 110 °C

Procedure

1.96 g of (3-bromo-5-trifluoromethylsulfanylpyridin-2-yl)-methylamine, 89 mg of acetylacetone copper(II), 0.27 g of acetylacetone, 2.34 g of cesium carbonate, 7 ml of NMP and 5 ml of aqueous ammonia (28%) were charged to a pressure-resistant reactor and stirred at 110° C. for 8.5 hours. Water was added to the reaction mixture cooled to room temperature, and the insoluble matter was filtered with celite (registered trademark), and then the filtered matter was washed with ethyl acetate, and the filtrate was extracted with ethyl acetate. The combined organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The resulting residue was applied to a silica gel column chromatography to obtain 1.18 g of N2-methyl-5-trifluoromethylsulfanylpyridine-2,3-diamine.

Workup

temperaturecooled to room temperature
filtrationthe insoluble matter was filtered with celite (registered trademark)
washthe filtered matter was washed with ethyl acetate
extractionthe filtrate was extracted with ethyl acetate
dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-0348384267e94c4f870e3c1b538a9756
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09156838B2

Reaction notes

Loading…