Sodium Azide → 4-(Azidomethyl)-2-(4-fluorophenyl)oxazole

HRID 1397356Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][CH:10]=[C:11]([CH2:13]I)[N:12]=2)=[CH:4][CH:3]=1.[N-:15]=[N+:16]=[N-:17].[Na+]>CN(C=O)C.CCOC(C)=O>[N:15]([CH2:13][C:11]1[N:12]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[O:9][CH:10]=1)=[N+:16]=[N-:17]

Participants

Conditions

Temperature: 70 °C

Procedure

A solution of 2-(4-fluorophenyl)-4-(iodomethyl)oxazole (1.2 g, 3.96 mmol) in dry DMF (10 mL) was added sodium azide (515 mg, 7.9 mmol) and the reaction mixture was heated to 70° C. for 8 h. The reaction mixture was allowed to cool down to room temperature and diluted with EtOAc. The mixture was extracted with EtOAc and the combined extracts were washed with water and brine, dried over anhydrous Na2SO4, and concentrated under reduced pressure to afford 4-(azidomethyl)-2-(4-fluorophenyl)oxazole (0.73 g, yield 85%) as a pale orange liquid, which was carried through without further purification. 1H NMR (400 MHz, CDCl3) δ 8.04-8.01 (m, 2H), 7.67 (s, 1H), 7.16-7.12 (m, 2H), 4.34 (s, 2H). MS (ESI) m/z: Calculated for C10H7FN4O: 218.06. found: 219.2 (M+H)+.

Workup

temperatureto cool down to room temperature
extractionThe mixture was extracted with EtOAc
washthe combined extracts were washed with water and brine
dry with materialdried over anhydrous Na2SO4
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-a1c5c0d0e76e4345be159783088417d8
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901156B2

Reaction notes

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