Triethylamine → HCID 86668043, compound

HRID 538333Notes

Reaction equation

HRID 538333 reaction equation
C1(P([N:15]=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.C(OC([C:23]1([C:31]2[CH:36]=[CH:35][N:34]=[C:33]([Br:37])[CH:32]=2)[CH2:28][O:27][C:26]([CH3:30])([CH3:29])[O:25][CH2:24]1)=O)C.C(N(CC)CC)C.C(OCC)(=O)C>C1(C)C=CC=CC=1.CCCCCC>[Br:37][C:33]1[CH:32]=[C:31]([C:23]2([NH2:15])[CH2:28][O:27][C:26]([CH3:30])([CH3:29])[O:25][CH2:24]2)[CH:36]=[CH:35][N:34]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 199401P,P-Diphenylphosphinic azideHCID 86668042HCID 86668042, compound

Product 1

HCID 86668043HCID 86668043, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8058HexaneSolvent

Conditions

Temperature
80 °C

Procedure

Dipheny phosphoryl azide (14.3 mL, 66.45 mmol) was added to a solution of 5-(2-bromo-pyridin-4-yl)-2,2-dimethyl-[1,3]dioxane-5-carboxylic acid ethyl ester (14.0 g, 44.3 mmol) and triethyl amine (17.24 ml, 133.0 mmol) in toluene (100 ml) at 0° C. The resultant reaction mixture was heated to 80° C. under constant stirring for 7 h. Reaction mixture was concentrated under reduced pressure to remove solvent completely. The residue obtained after concentration was dissolved in THF (100 ml) and cooled to 0° C. 2 N aq. NaOH solution was added drop wise and stirred for 30 min at rt. Reaction mixture was concentrated under reduced pressure to remove THF and the residue obtained was extracted with ethylacetate. Organic layer was washed with water, brine and dried over anhy. Na2SO4. Organic layer was concentrated under reduced pressure to obtain furnished brownish oily material which was solidified at low temperature (<10° C.). Yield=9.5 g (75%). TLC (50% ethyl acetate in hexane) Rf=0.15; LCMS: RtH7=0.083; [M+1]+=287.0 and 289.0.

Workup

  1. customThe resultant reaction mixture
  2. customReaction mixture
  3. concentrationwas concentrated under reduced pressure
  4. customto remove solvent completely
  5. customThe residue obtained
  6. concentrationafter concentration
  7. dissolutionwas dissolved in THF (100 ml)
  8. temperaturecooled to 0° C
  9. addition2 N aq. NaOH solution was added drop wise
  10. stirringstirred for 30 min at rt
  11. customReaction mixture
  12. concentrationwas concentrated under reduced pressure
  13. customto remove THF
  14. customthe residue obtained
  15. extractionwas extracted with ethylacetate
  16. washOrganic layer was washed with water, brine
  17. customdried over anhy
  18. concentrationOrganic layer was concentrated under reduced pressure
  19. customto obtain
  20. customfurnished brownish oily material which
  21. customwas solidified at low temperature (<10° C.)

Sources & evidence

ORD record
ord-c60584cdce4b4f87932152a8ebd9e4af
Source dataset
uspto-grants-2014_10
Patent number
US08865712B2

Reaction notes

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