Water → N4-Benzyl-2-chloro-6-trifluoromethyl-pyridine-3,4-diamine

HRID 639704Notes

Reaction equation

Br[C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[N:5]=[C:4]([Cl:12])[C:3]=1[NH2:13].[F-].[Cs+].[CH2:16]([NH2:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O>CS(C)=O>[CH2:16]([NH:23][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[N:5]=[C:4]([Cl:12])[C:3]=1[NH2:13])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 150 °C

Procedure

4-Bromo-2-chloro-6-trifluoromethyl-pyridin-3-ylamine (84 g, 300 mmol) was stirred in 500 ml DMSO in the presence of caesium fluoride (46.3 g, 305 mmol) and benzylamine (66.6 ml, 610 mmol). The resulting brown suspension was heated at 150° C. for 16 h. Added to the cooled suspension was 1500ml water and the mixture extracted with 2×500 ml diethyl ether. The combined organic extracts were dried (MgSO4), concentrated in vacuo and purified by column chromatography on silica, eluting with Hept:EtOAc, 4:1 to 2:1 to give the title compound (15.8 g, 17%) as a pale brown solid. The undesired isomer was similarly isolated as a brown oil (51.0 g, 48%).

Workup

additionAdded to the cooled suspension
extractionthe mixture extracted with 2×500 ml diethyl ether
dry with materialThe combined organic extracts were dried (MgSO4)
concentrationconcentrated in vacuo
custompurified by column chromatography on silica
washeluting with Hept

Sources & evidence

ORD record: ord-443654e2320d488987e2d870cce336c6
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07691877B2

Reaction notes

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