2-Bromo-5-methylpyridine → HCID 178426495, compound

HRID 707239Notes

Reaction equation

[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:4][CH2:3]1.Br[C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][N:18]=1.C([O-])(=O)C.[Cs+]>CS(C)=O.[OH-].[Na+].[Cu]>[C:11]([O:10][C:9](=[O:15])[NH:8][C@H:5]1[CH2:6][CH2:7][C@H:2]([NH:1][C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][N:18]=2)[CH2:3][CH2:4]1)([CH3:12])([CH3:14])[CH3:13]

Participants

Conditions

Temperature: 100 °C

Procedure

Tert-butyl trans-4-aminocyclohexylcarbamate (1.9965 g, 9.32 mmol), 2-bromo -5-methylpyridine (1.923 g, 11.18 mmol), copper (0.047 g, 0.745 mmol), and cesium acetate (11.09 g, 57.8 mmol) were suspended in dry DMSO (11.65 ml) and stirred at 100° C. for 22 hours. The reaction was allowed to cool to room temperature. The reaction mixture was diluted with 1N sodium hydroxide and extracted with ethyl acetate. The organic extract was washed with water, brine, dried over magnesium sulfate and concentrated in vacuo. The crude product was adsorbed onto a plug of silica gel and chromatographed through a Biotage SNAP HP-silica gel column (100 g), eluting with a gradient of 10% to 100% EtOAc in hexane, to provide tert-butyl(trans-4-((5-methylpyridin-2-yl)amino)cyclohexyl)carbamate (0.9695 g, 3.17 mmol, 34.1% yield).

Workup

temperatureto cool to room temperature
extractionextracted with ethyl acetate
extractionThe organic extract
washwas washed with water, brine
dry with materialdried over magnesium sulfate
concentrationconcentrated in vacuo
customchromatographed through a Biotage SNAP HP-silica gel column (100 g)
washeluting with a gradient of 10% to 100% EtOAc in hexane

Sources & evidence

ORD record: ord-05c95bf6e26b403f9c86be84b6938cbe
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09174992B2

Reaction notes

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