Potassium Carbonate → 1,1-Dimethylethyl 4-(5-bromo-2-pyridinyl)-1,4-diazepane-1-carboxylate

HRID 1640423Notes

Reaction equation

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

Participants

Conditions

Temperature: 150 °C

Procedure

1.03 g (5 mmol) of 1,1-dimethylethyl 1,4-diazepane-1-carboxylate, 1.19 g (5 mmol) of 2,5-dibromopyridine and 0.7 g (5 mmol) of potassium carbonate suspended in 0.90 ml of dimethyl sulfoxide (DMSO) are introduced into an autoclave. The mixture is heated at 150° C. for 22 hours. The reaction mixture is allowed to cool to room temperature, it is taken up in ethyl acetate, and the organic solution is washed with water and then brine, and dried over sodium sulfate. The filtrate is concentrated under reduced pressure and the residue thus obtained is purified by chromatography on silica gel, eluting with a 99.5/0.5 mixture of dichloromethane and methanol. 1.63 g of product are obtained in the form of an oil, and are used without further purification in the following step.

Workup

additionare introduced into an autoclave
temperatureto cool to room temperature
washthe organic solution is washed with water
dry with materialbrine, and dried over sodium sulfate
concentrationThe filtrate is concentrated under reduced pressure
customthe residue thus obtained
customis purified by chromatography on silica gel
washeluting with a 99.5/0.5 mixture of dichloromethane and methanol

Sources & evidence

ORD record: ord-e650480134f94486a6779671c8dd79b3
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08114866B2

Reaction notes

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