Dimethylformamide → HCID 23371882, compound

HRID 1900081Notes

Reaction equation

HRID 1900081 reaction equation
Br[C:2]1[N:7]=[CH:6][C:5]([N:8]2[CH2:12][CH:11]([CH2:13][O:14][CH3:15])[O:10][C:9]2=[O:16])=[CH:4][CH:3]=1.CN(C)[CH:19]=[O:20]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[O:20]1[C:19]2([CH2:6][CH2:5][C:4]([C:2]3[N:7]=[CH:6][C:5]([N:8]4[CH2:12][CH:11]([CH2:13][O:14][CH3:15])[O:10][C:9]4=[O:16])=[CH:4][CH:3]=3)=[CH:3][CH2:2]2)[O:10][CH2:11][CH2:12]1

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 23371856HCID 23371856, compound

Product 1

HCID 23371882HCID 23371882, compound

Reagents, catalysts & solvents 1

HCID 178418476HCID 178418476, compoundCatalyst

Procedure

A suspension of 8.9 g of (RS)-3-(6-bromo-pyridin-3-yl)-5-methoxymethyl-oxazolidin-2-one, 6.5 g of 8-tributyl-stannyl-1,4-dioxaspiro[4,5]dec-7-ene and 1.4 g of bis(triphenylphosphine)palladium(II) dichloride in 40 ml of dimethylformamide was stirred at 85° under argon for 22 h. Then, the mixture was cooled, filtered over a Celite® pad, the filter cake was washed with a large amount of ethyl acetate and the organic phase was washed several times with semi-saturated sodium chloride solution. The aqueous phases were extracted with ethyl acetate, the organic phases were combined, concentrated to a volume of 250 ml, treated with 250 ml of saturated potassium fluoride solution and stirred for 30 minutes. The mixture was again filtered over a Celite® pad, the phases were separated and the aqueous phase was extracted with ethyl acetate. The organic phases were combined, dried with magnesium sulfate, concentrated and chromatographed over silica gel 60 with diethyl ether as the eluent. There were obtained 1.2 g of (RS)-3-[6-(1,4-dioxa-spiro[4,5]dec-7-en-8-yl)-pyridin-3-yl]-5-methoxymethyl-oxazolidin-2-one. 1H-nmr (CDCl3) ppm: 8.48 (s, 1H), 8.19 (d, 1H), 7.56 (d,1H), 6.50 (m, 1H), 4.79 (m, 1H), 4.12 (t, 1H), 4.02 (s, 4H), 3.98 (t, 1H), 3.64 (m, 2H), 3.44 (s, 3H), 2.80 (m, 2H), 2.52 (m, 2H), 1.96 (t, 2H).

Workup

  1. temperatureThen, the mixture was cooled
  2. filtrationfiltered over a Celite® pad
  3. washthe filter cake was washed with a large amount of ethyl acetate
  4. washthe organic phase was washed several times with semi-saturated sodium chloride solution
  5. extractionThe aqueous phases were extracted with ethyl acetate
  6. concentrationconcentrated to a volume of 250 ml
  7. additiontreated with 250 ml of saturated potassium fluoride solution
  8. stirringstirred for 30 minutes
  9. filtrationThe mixture was again filtered over a Celite® pad
  10. customthe phases were separated
  11. extractionthe aqueous phase was extracted with ethyl acetate
  12. dry with materialdried with magnesium sulfate
  13. concentrationconcentrated
  14. customchromatographed over silica gel 60 with diethyl ether as the eluent

Sources & evidence

ORD record
ord-69062331dba143ef828f6d84acaa3574
Source dataset
uspto-grants-1996_11
Patent number
US05574055

Reaction notes

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