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

HRID 1640423
Notes
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Reaction equation

HRID 1640423 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 693532,5-DibromopyridineHCID 2756058Tert-butyl 1,4-diazepane-1-carboxylate

Product 1

HCID 602095661,1-Dimethylethyl 4-(5-bromo-2-pyridinyl)-1,4-diazepane-1-carboxylateYield 91.5%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent
HCID 8857
Ethyl Acetate
Solvent

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

  1. additionare introduced into an autoclave
  2. temperatureto cool to room temperature
  3. washthe organic solution is washed with water
  4. dry with materialbrine, and dried over sodium sulfate
  5. concentrationThe filtrate is concentrated under reduced pressure
  6. customthe residue thus obtained
  7. customis purified by chromatography on silica gel
  8. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes