2-Bromopyridine → HCID 19963216, compound

HRID 1977062Notes

Reaction equation

HRID 1977062 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:12][N:7]2[CH2:8][CH2:9][NH:10][CH2:11][CH:6]2[CH2:5][CH2:4]1.Br[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)CC(C)C>[OH:1][CH2:2][CH:3]1[CH2:12][N:7]2[CH2:8][CH2:9][N:10]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=3)[CH2:11][CH:6]2[CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 79732-BromopyridineHCID 10340Sodium CarbonateHCID 12985539(Octahydro-1H-pyrido[1,2-A]pyrazin-7-YL)methanol

Product 1

HCID 19963216HCID 19963216, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 31260Isoamyl AlcoholSolvent

Procedure

A mixture of 1.0 g (5.9 mmol) of (7RS,9aSR)-7-hydroxymethyl-2,3,4,6,7,8,9,9a-octahydro-1H-pyrido[1,2-a]pyrazine (U.S. Pat. No. 5,326,874); 4.6 g (29 mmol) of 2-bromopyridine, 1.5 g (14 mmol) of sodium carbonate and 50 mL of isoamyl alcohol were refluxed for 18 h. The mixture was cooled to room temperature, filtered, and concentrated in vacuo. The residue was dissolved in ethyl acetate and washed with saturated sodium carbonate. The organic layer was dried (magnesium sulfate), filtered and evaporated, and the crude product was purified by flash chromatography on silica gel eluting first with chloroform followed by 95:5 chloroform:methanol to give 0.61 g (42%) of the title compound. 13C NMR (base, CDCl3): δ26.8, 29.0, 39.0, 45.1, 50.7, 54.8, 58.7, 60.8, 66.0, 107.1, 113.3, 137.5, 147.9, 159.3.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with saturated sodium carbonate
  5. dry with materialThe organic layer was dried (magnesium sulfate)
  6. filtrationfiltered
  7. customevaporated
  8. customthe crude product was purified by flash chromatography on silica gel eluting first with chloroform

Sources & evidence

ORD record
ord-e96f85fb8cdf40dda905c8fb2be19d0c
Source dataset
uspto-grants-2001_05
Patent number
US06231833B1

Reaction notes

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