2-Bromopyridine → HCID 15351904, compound

HRID 1858354Notes

Reaction equation

HRID 1858354 reaction equation
[H-].[Na+].[O:3]1[C@@H:15]2[C@@:16]34[CH2:18][CH2:19][N:20]([CH3:21])[C@@H:10]([C@@H:11]3[CH:12]=[CH:13][C@@H:14]2[OH:22])[CH2:9][C:8]2=[C:17]4[C:4]1=[C:5]([O:23][CH2:24][O:25][CH3:26])[CH:6]=[CH:7]2.Br[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=1>CN(C=O)C>[O:3]1[C@@H:15]2[C@@:16]34[CH2:18][CH2:19][N:20]([CH3:21])[C@@H:10]([C@@H:11]3[CH:12]=[CH:13][C@@H:14]2[O:22][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=2)[CH2:9][C:8]2=[C:17]4[C:4]1=[C:5]([O:23][CH2:24][O:25][CH3:26])[CH:6]=[CH:7]2

Participants

5

Reactant 3

HCID 79732-BromopyridineHCID 24758Sodium hydrideHCID 10860472HCID 10860472, compound

Product 1

HCID 15351904HCID 15351904, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

NaH (0.432 g, 18 mmol) is stirred with absolute DMF (12 ml) at ambient temperature and then 4,5α-epoxy-3-methoxymethoxy-17-methyl-morphinan-7-en-6α-ol (1.9764 g, 6 mmol) in DMF (12 ml) is added. After the development of gas has ceased, a solution of 2-bromopyridine in absolute DMF (8 ml) is added at RT. After 3 hours at RT this reaction mixture is poured onto H2O (100 ml) and extracted 3 times with CH2Cl2 (60 ml). The combined organic phases are dried with Ha2SO4, concentrated by rotary evaporation and the residue is purified by flash chromatography (90 g silica gel, CH2Cl2 /MeOH=9/1).

Workup

  1. additionAfter 3 hours at RT this reaction mixture is poured onto H2O (100 ml)
  2. extractionextracted 3 times with CH2Cl2 (60 ml)
  3. customThe combined organic phases are dried with Ha2SO4
  4. concentrationconcentrated by rotary evaporation
  5. customthe residue is purified by flash chromatography (90 g silica gel, CH2Cl2 /MeOH=9/1)

Sources & evidence

ORD record
ord-e13fbcb0fefa49abbeb664d7d23f6c08
Source dataset
uspto-grants-2000_11
Patent number
US06150524

Reaction notes

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