Tert-Butyl nitrite → HCID 86699007, compound

HRID 1520014Notes

Reaction equation

HRID 1520014 reaction equation
N(OC(C)(C)C)=O.[F:8][C:9]1[CH:10]=[C:11]([CH:13]=[CH:14][C:15]=1[C:16]([N:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1)=[O:17])[NH2:12].[N:24]([Si](C)(C)C)=[N+:25]=[N-]>CCOC(C)=O>[N:12]([C:11]1[CH:13]=[CH:14][C:15]([C:16]([N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)=[O:17])=[C:9]([F:8])[CH:10]=1)=[N+:24]=[N-:25]

Participants

5

Reactant 3

HCID 10906Tert-Butyl nitriteHCID 78378AzidotrimethylsilaneHCID 61708912HCID 61708912, compound

Product 1

HCID 86699007HCID 86699007, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-10 °C

Procedure

Tert-butyl nitrite (0.16 mL; 1.34 mmol; 1.5 eq.) was added to a solution of 3-fluoro-4-(morpholin-4-ylcarbonyl)aniline (200 mg; 0.89 mmol; 1.0 eq.) in AcOEt (6 mL) maintained at −10° C. The reaction mixture was stirred at −10° C. for 10 minutes before the addition of azidotrimethylsilane (0.14 mL; 1.07 mmol; 1.2 eq.). Reaction mixture was stirred at RT for 2 hours and concentrated under reduced pressure to give the title compound as a pale orange oil (220 mg, 99%). 1H NMR (300 MHz, DMSO-d6): δ: 7.45 (t, J=8.0 Hz, 1H), 7.15 (dd, J=11.0 Hz, 2.1 Hz, 1H), 7.06 (dd, J=8.0 Hz, 2.1 Hz, 1H), 3.64-3.63 (m, 4H), 3.52 (t, J=4.6 Hz, 2H), 3.23 (t, J=4.6 Hz, 2H). MS (ES+): 2521.1; Rt 1.02 min (purity=92%).

Workup

  1. customReaction mixture
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a49c5026e25b44958b850e67ba8aeddf
Source dataset
uspto-grants-2015_07
Patent number
US09073892B2

Reaction notes

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