Water → 2-Bromo-5-((2-chloropyridin-4-yl)oxy)pyrazine

HRID 1049274Notes

Reaction equation

HRID 1049274 reaction equation
Br[C:2]1[CH:7]=[N:6][C:5]([Br:8])=[CH:4][N:3]=1.[Cl:9][C:10]1[CH:15]=[C:14]([OH:16])[CH:13]=[CH:12][N:11]=1.C([O-])([O-])=O.[Cs+].[Cs+].O>CN(C=O)C>[Br:8][C:5]1[CH:4]=[N:3][C:2]([O:16][C:14]2[CH:13]=[CH:12][N:11]=[C:10]([Cl:9])[CH:15]=2)=[CH:7][N:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 114704212,5-dibromopyrazineHCID 178516507HCID 178516507, compound

Product 1

HCID 904031962-Bromo-5-((2-chloropyridin-4-yl)oxy)pyrazineYield 84.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 2,5-dibromopyrazine (2.42 g, 10.2 mmol), 2-chloro-4-hydroxy pyridine (1.2 g, 9.3 mmol) and Cs2CO3 (3.02 g, 9.26 mmol) in DMF (15 mL) was heated at 70° C. for 16 h with stirring. The mixture was poured into water (150 mL) and stirred for 15 min. The resultant precipitate was collected by filtration, washed with water (4×4 mL) and dried in vacuo to provide 2-bromo-5-((2-chloropyridin-4-yl)oxy)pyrazine (2.24 g, 84%) as an off-white solid. MS (ESI) m/z: 285.9/287.9 (M+H+).

Workup

  1. stirringstirred for 15 min
  2. filtrationThe resultant precipitate was collected by filtration
  3. washwashed with water (4×4 mL)
  4. customdried in vacuo

Sources & evidence

ORD record
ord-83f9d839ee5e455d96134f8a46f17baa
Source dataset
uspto-grants-2016_07
Patent number
US09382228B2

Reaction notes

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