Water → 4-(5-Bromopyridin-2-yl)-1,4-oxazepane

HRID 57570

Reaction equation

HRID 57570 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](Cl)=[N:6][CH:7]=1.[O:9]1[CH2:15][CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.C([O-])([O-])=O.[K+].[K+].O>CN1C(=O)CCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:12]2[CH2:13][CH2:14][CH2:15][O:9][CH2:10][CH2:11]2)=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27344145-Bromo-2-chloropyridineHCID 218732751,4-Oxazepane

Product 1

HCID 629674864-(5-Bromopyridin-2-yl)-1,4-oxazepaneYield 92.7%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

The solution of 5-bromo-2-chloropyridine (1.5 g, 7.8 mmol), 1,4-oxazepane (1.29 g, 9.36 mmol) and K2CO3 in 15 mL of NMP was stirred at 120° C. overnight. The mixture was added to 150 mL of water, washed with EA, dried over Na2SO4, and the volatiles were removed in vacuo to give 1.86 g of 4-(5-bromopyridin-2-yl)-1,4-oxazepane. MS(m/z)=259 (M+H)+.

Workup

  1. washwashed with EA
  2. dry with materialdried over Na2SO4
  3. customthe volatiles were removed in vacuo

Sources & evidence

ORD record
ord-937f5186029b471ba0aeeec94578dc8a
Source dataset
uspto-grants-2016_09
Patent number
US09434726B2

Linked notes

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