Benzyl azide → ethyl 2-(1-(4-fluorobenzyl)-1H-1,2,3-triazol-4-yl)-4-methylthiazole-5-carboxylate

HRID 2381805Notes

Reaction equation

HRID 2381805 reaction equation
C(N=[N+]=[N-])C1C=CC=CC=1.[N:11]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1)=[N+:12]=[N-:13].[C:22]([C:24]1[S:25][C:26]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[C:27]([CH3:29])[N:28]=1)#[CH:23]>>[F:21][C:18]1[CH:19]=[CH:20][C:15]([CH2:14][N:11]2[CH:23]=[C:22]([C:24]3[S:25][C:26]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[C:27]([CH3:29])[N:28]=3)[N:13]=[N:12]2)=[CH:16][CH:17]=1

Participants

4

Reactant 3

HCID 12152Benzyl azideHCID 112058641-(Azidomethyl)-4-fluorobenzeneHCID 59179676Ethyl 2-ethynyl-4-methylthiazole-5-carboxylate

Product 1

HCID 59179694ethyl 2-(1-(4-fluorobenzyl)-1H-1,2,3-triazol-4-yl)-4-methylthiazole-5-carboxylateYield 62%

Procedure

Following the procedure as described in Example 2, making variations as necessary to replace benzylazide with 1-(azidomethyl)-4-fluorobenzene to react with ethyl 2-ethynyl-4-methylthiazole-5-carboxylate, the title compound was obtained as a white solid in 62% yield: 1H NMR (300 MHz, CDCl3) δ 7.98 (s, 1H), 7.32-7.23 (m, 2H), 7.05-6.94 (m, 2H), 5.49 (s, 2H), 4.51 (q, J=7.1 Hz, 2H), 2.62 (s, 3H), 1.29 (t, J=7.1 Hz, 3H); MS (ES+) m/z 347.3 (M+1).

Sources & evidence

ORD record
ord-0ba681eded554ba8818a6f2fb7d75d1f
Source dataset
uspto-grants-2012_09
Patent number
US08258160B2

Reaction notes

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