Dimethylformamide → HCID 21114570, compound

HRID 1767754Notes

Reaction equation

HRID 1767754 reaction equation
[H-].[Na+].[N:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1CO.Br[C:12]1[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][N:13]=1.CN(C)[CH:21]=[O:22]>>[Br:18][C:15]1[CH:14]=[N:13][C:12]([O:22][CH2:21][C:7]2[CH:8]=[N:3][CH:4]=[CH:5][CH:6]=2)=[CH:17][CH:16]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 11474PiconolHCID 24758Sodium hydrideHCID 693532,5-Dibromopyridine

Product 1

HCID 21114570HCID 21114570, compoundYield 46%

Conditions

Temperature
100 °C

Procedure

Sodium hydride (144 mg, 3.6 mmol) was added to a solution of 2-pyridine-methanol (361 mg, 3.3 mmol) in dimethylformamide (5 ml) and stirred for 20 minutes. 2,5-Dibromopyridine (711 mg, 3.0 mmol) was added, the reaction was heated to 100° C. for 10 hours, before the reaction was cooled and the solvents removed in vacuo. 2.0 N aqueous sodium hydroxide solution (5 ml) was added, the aqueous layer was extracted with ethyl acetate which was washed with and concentrated in vacuo. Purification by flash chromatography on silica gel, eluting with 5% ethyl acetate in isohexane, yielded 3-bromo-6-(3-pyridylmethoxy)pyridine (366 mg, 46% yield) as an off-white solid:

Workup

  1. temperaturewas cooled
  2. customthe solvents removed in vacuo
  3. addition2.0 N aqueous sodium hydroxide solution (5 ml) was added
  4. extractionthe aqueous layer was extracted with ethyl acetate which
  5. washwas washed with and
  6. concentrationconcentrated in vacuo
  7. customPurification by flash chromatography on silica gel
  8. washeluting with 5% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-9b1a3b15c9eb4c64ae413f94fb709acb
Source dataset
uspto-grants-2007_06
Patent number
US07235559B1

Reaction notes

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