Sodium Carbonate → HCID 86668047, compound

HRID 538337Notes

Reaction equation

HRID 538337 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([C:8]2([CH2:15]O)[NH:13][C:12](=[O:14])[CH2:11][O:10][CH2:9]2)[CH:5]=[CH:4][N:3]=1.C([O-])([O-])=O.[Na+].[Na+].C(N(S(F)(F)[F:29])CC)C>C1COCC1>[Br:1][C:2]1[CH:7]=[C:6]([C:8]2([CH2:15][F:29])[NH:13][C:12](=[O:14])[CH2:11][O:10][CH2:9]2)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 10340Sodium Carbonate2×HCID 123472(Diethylamino)sulfur trifluorideHCID 86668046HCID 86668046, compound

Product 1

HCID 86668047HCID 86668047, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 5-(2-bromo-pyridin-4-yl)-5-hydroxymethyl-morpholin-3-one (3.25 g, 11.0 mmol), Na2CO3 (3.5 g, 13.06 mmol) in dry THF (15 ml) was added diethylaminosulfur trifluoride (2.25 ml, 17.0 mmol) at 0° C. The reaction mixture was allowed to warm to rt and stirred for 2 h. Solid Na2CO3 (3.5 g) was again added to the reaction mixture and stirred for 4 h at rt. Solids present in the reaction mixture filtered through Buchner funnel. Filtrate was concentrated under reduced pressure and the crude product was purified by column chromatography using 5% methanol in DCM to obtain title compound as a pale yellow solid. Yield=2.1 g (66%). TLC (50% ethyl acetate in hexane) Rf=0.17; LCMS: RtH7=0.201; [M+1]+=289 and 291; HPLC: RtH9=5.171 min. (50%) and 5.063 (21%).

Workup

  1. stirringstirred for 4 h at rt
  2. filtrationSolids present in the reaction mixture filtered through Buchner funnel
  3. concentrationFiltrate was concentrated under reduced pressure
  4. customthe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-500aad2589ad43e8a8951322e639961d
Source dataset
uspto-grants-2014_10
Patent number
US08865712B2

Reaction notes

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