Sodium Azide → HCID 86677882, compound

HRID 1499960Notes

Reaction equation

HRID 1499960 reaction equation
CS(O[CH:6]([C:16]1[C:21]([F:22])=[C:20]([Cl:23])[CH:19]=[C:18]([C:24](=[O:26])[CH3:25])[C:17]=1[O:27][CH2:28][CH3:29])[CH2:7][O:8][Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10])(=O)=O.[N-:30]=[N+:31]=[N-:32].[Na+]>CS(C)=O.[Cl-].[Na+].O>[N:30]([CH:6]([C:16]1[C:17]([O:27][CH2:28][CH3:29])=[C:18]([C:24](=[O:26])[CH3:25])[CH:19]=[C:20]([Cl:23])[C:21]=1[F:22])[CH2:7][O:8][Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10])=[N+:31]=[N-:32]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 86677881HCID 86677881, compound

Product 1

HCID 86677882HCID 86677882, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
50 °C

Procedure

1-(3-Acetyl-5-chloro-2-ethoxy-6-fluorophenyl)-2-{[tert-butyl(dimethyl)silyl]oxy}ethyl methanesulfonate (0.83 g, 1.77 mmol) (from Step 4) was stirred in dimethyl sulfoxide (10 mL) and sodium azide (0.12 g, 1.8 mmol) was added. The mixture was heated to 50° C. for 1 hour and cooled to rt. The mixture was poured into brine and extracted with ethyl acetate. The extracts were dried over sodium sulfate, filtered and evaporated to give the desired compound 736 mg, 100%. LCMS calculated for C18H27ClFN3O3SiNa (M+Na)+: m/z=438.1; found: 438.1.

Workup

  1. temperaturecooled to rt
  2. extractionextracted with ethyl acetate
  3. dry with materialThe extracts were dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-5ac83b473dd349759a624d355089f437
Source dataset
uspto-grants-2015_12
Patent number
US09199982B2

Reaction notes

Loading…