2-Bromopyridine → HCID 117858320, compound

HRID 1486294Notes

Reaction equation

HRID 1486294 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[CH2:9][OH:10].[H-].[Na+].Br[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1>O1CCCC1.O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[CH2:9][O:10][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1

Participants

6

Reactant 3

HCID 79732-BromopyridineHCID 24758Sodium hydrideHCID 879212,6-Difluorobenzyl alcohol

Product 1

HCID 117858320HCID 117858320, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2 ml (18.0 mmol) of (2,6-difluorophenyl)methanol in 15 ml of dry tetrahydrofuran stirred at 0° C. was admixed with 865.9 mg (21.6 mmol) of sodium hydride (60% in mineral oil), followed by 1.72 ml (18.0 mmol) of 2-bromopyridine. The resulting solution was stirred at room temperature for 15 h. The reaction mixture was diluted with water (15 ml) and extracted with dichloromethane (2×20 ml). The organic phase was removed, dried with a phase separation cartridge and concentrated under reduced pressure. The residue was purified by flash chromatography using a prepacked silica gel cartridge (eluent:cyclohexane-ethyl acetate 10:1 to 1:1), which gave 800 mg (15% of theory, 77% pure) of the target compound.

Workup

  1. extractionextracted with dichloromethane (2×20 ml)
  2. customThe organic phase was removed
  3. customdried with a phase separation cartridge
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash chromatography
  6. customgave 800 mg (15% of theory, 77% pure) of the target compound

Sources & evidence

ORD record
ord-f85860e207024996a53295778a55905b
Source dataset
uspto-grants-2016_08
Patent number
US09422285B2

Reaction notes

Loading…