Sodium Azide → HCID 86652104, compound

HRID 1845115Notes

Reaction equation

HRID 1845115 reaction equation
CS(O[C@H:6]([C:16]1[CH:17]=[N:18][C:19]([CH:22]([F:24])[F:23])=[CH:20][CH:21]=1)[CH2:7][O:8][Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10])(=O)=O.[N-:25]=[N+:26]=[N-:27].[Na+]>CN(C=O)C>[N:25]([C@@H:6]([C:16]1[CH:21]=[CH:20][C:19]([CH:22]([F:24])[F:23])=[N:18][CH:17]=1)[CH2:7][O:8][Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10])=[N+:26]=[N-:27]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 86652105HCID 86652105, compound

Product 1

HCID 86652104HCID 86652104, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of (R)-2-(tert-Butyldimethylsilyloxy)-1-(6-(difluoromethyl)pyridin-3-yl)ethyl methanesulfonate (2.24 g, 5.87 mmol) in dry DMF (15 mL) was added NaN3 (0.45 g, 7.05 mmol) and the resulting reaction mixture was heated at 60° C. for 2 h. After completion of the reaction the reaction mixture was treated with ice-cold water and extracted with Et2O. The organic layer was dried over anhydrous Na2SO4 and the solvents were evaporated in vacuo to afford the title compound (1.63 g, 85% yield). MS: 328 [M+1]+; 1H-NMR (300 MHz, CDCl3): 8.60 (s, 1H), 7.82 (d, 1H, J=8.3 Hz), 7.64 (d, 1H, J=8.3 Hz), 6.64 (t, 1H, J=55.7 Hz), 4.65-4.70 (m 1H), 3.80-3.86 (m, 2H), 0.89 (s, 9H), 0.04-0.06 (m, 61-1).

Workup

  1. customthe resulting reaction mixture
  2. customAfter completion of the reaction the reaction mixture
  3. additionwas treated with ice-cold water
  4. extractionextracted with Et2O
  5. dry with materialThe organic layer was dried over anhydrous Na2SO4
  6. customthe solvents were evaporated in vacuo

Sources & evidence

ORD record
ord-eb72429ff21548df96cad9341caab029
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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