Sodium hydride → (2,5-Dimethyl-4-pyridin-3-yl-imidazol-1-yl)-carbamic acid tert-butyl ester

HRID 1502578Notes

Reaction equation

HRID 1502578 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([CH3:13])=[C:5]([C:7]2[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=2)[N:6]=1.[H-].[Na+].[C:16]([O:20][C:21]([N:23]1C(C2C=CC(C#N)=CC=2)O1)=[O:22])([CH3:19])([CH3:18])[CH3:17]>>[C:16]([O:20][C:21](=[O:22])[NH:23][N:3]1[C:4]([CH3:13])=[C:5]([C:7]2[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=2)[N:6]=[C:2]1[CH3:1])([CH3:19])([CH3:18])[CH3:17]

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 2725038N-Boc-3-(4-cyanophenyl)oxaziridineHCID 674990253-(2,5-dimethyl-1H-imidazol-4-yl)pyridine

Product 1

HCID 67499760(2,5-Dimethyl-4-pyridin-3-yl-imidazol-1-yl)-carbamic acid tert-butyl ester

Procedure

3-(2,5-Dimethyl-1H-imidazol-4-yl)-pyridine (0.035 g, 0.220 mmol) was weighed into an oven dried, nitrogen swept 10 mL round bottomed flask. Tetrahydrofuran (THF, 1 mL) was added via syringe and the resulting slurry cooled on an ice bath under nitrogen and treated with sodium hydride (0.0097 g, 0.242 mmol 60% dispersion in oil) with stirring. After 10 minutes, 3-(4-cyano-phenyl)-oxaziridine-2-carboxylic acid tert-butyl ester (0.052 g, 0.212 mmol) was added as a solid and the thick yellow slurry allowed to warm to room temperature and stir for 2 hours. The crude reaction mixture was loaded directly onto a flash silica gel column and eluted with CH2Cl2:MeOH/10:1 giving (2,5-dimethyl-4-pyridin-3-yl-imidazol-1-yl)-carbamic acid tert-butyl ester as a light yellow oil as a 5:1 mixture with its regioisomer (0.027 g, 46%): IR (film) 3389, 2978, 2930, 1730, 1478, 1275, 1252, 1156, 1017, 951, 711, 573 cm−1; 1H NMR (300 MHz, DMSO, Major isomer) δ 10.41 (s, 1H), 8.81 (s, 1H), 8.39 (s, 1H), 7.95 (d, J=8.0 Hz, 1H), 7.44-7.28 (m, 1H), 2.21 (s, 3H), 2.18 (s, 3H), 1.46 (s, 9H); ESIMS m/z 289 [(M+H)]+ and 287 [(M−H)]−.

Workup

  1. customdried
  2. additionTetrahydrofuran (THF, 1 mL) was added via syringe
  3. temperaturethe resulting slurry cooled on an ice bath under nitrogen
  4. stirringstir for 2 hours
  5. customThe crude reaction mixture
  6. washeluted with CH2Cl2

Sources & evidence

ORD record
ord-dfd97e06875f4b779d9294ece4eeb7e1
Source dataset
uspto-grants-2015_12
Patent number
US09210931B2

Reaction notes

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