Ethyl Acetate → HCID 58576452, compound

HRID 75105Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][N:3]=1.[NH2:12][CH:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CS(C)=O.O>[F:9][C:8]([F:11])([F:10])[C:5]1[CH:6]=[CH:7][C:2]([NH:12][CH:13]2[CH2:14][CH2:15][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:17][CH2:18]2)=[N:3][CH:4]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 0.678 g (3 mmol) of 2-bromo-5-(trifluoromethyl)pyridine, 0.901 g (4.5 mmol) of tert-butyl 4-aminopiperidine-1-carboxylate and 0.829 g (6 mmol) of potassium carbonate in 5 ml of dimethyl sulphoxide is heated at 100° C. for 20 hours. The mixture is cooled to ambient temperature and then 50 ml of ethyl acetate and 15 ml of water are added. The organic phase is separated by settling and washed twice with 15 ml of water and then with 15 ml of a saturated aqueous sodium chloride solution. It is dried over sodium sulphate and evaporated under vacuum. The product is purified by chromatography on silica gel, elution being carried out with a 20:80 and then 30:70 mixture of ethyl acetate and cyclohexane in order to obtain 0.864 g (2.5 mmol) of product in the form of a white solid.

Workup

temperatureThe mixture is cooled to ambient temperature
customThe organic phase is separated
washwashed twice with 15 ml of water
dry with materialIt is dried over sodium sulphate
customevaporated under vacuum
customThe product is purified by chromatography on silica gel, elution
addition30:70 mixture of ethyl acetate and cyclohexane in order

Sources & evidence

ORD record: ord-9d9fb918e31e49c8ae43b43b85cd4bb9
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08835418B2

Reaction notes

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