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

HRID 2381807Notes

Reaction equation

HRID 2381807 reaction equation
C(N=[N+]=[N-])C1C=CC=CC=1.[N:11]([CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1)=[N+:12]=[N-:13].[C:23]([C:25]1[S:26][C:27]([C:31]([O:33][CH2:34][CH3:35])=[O:32])=[C:28]([CH3:30])[N:29]=1)#[CH:24]>>[F:22][C:19]1[CH:20]=[CH:21][C:16]([CH2:15][CH2:14][N:11]2[CH:24]=[C:23]([C:25]3[S:26][C:27]([C:31]([O:33][CH2:34][CH3:35])=[O:32])=[C:28]([CH3:30])[N:29]=3)[N:13]=[N:12]2)=[CH:17][CH:18]=1

Participants

4

Reactant 3

HCID 12152Benzyl azideHCID 59179676Ethyl 2-ethynyl-4-methylthiazole-5-carboxylateHCID 596674281-(2-Azidoethyl)-4-fluorobenzene

Product 1

HCID 59179678ethyl 2-(1-(4-fluorophenethyl)-1H-1,2,3-triazol-4-yl)-4-methylthiazole-5-carboxylateYield 82%

Procedure

Following the procedure as described in Example 2, making variations as necessary to replace benzylazide with 1-(2-azidoethyl)-4-fluorobenzene to react with ethyl 2-ethynyl-4-methylthiazole-5-carboxylate, the title compound was obtained as a white solid in 82% yield: 1H NMR (300 MHz, CDCl3) δ 7.87 (s, 1H), 7.09-6.98 (m, 2H), 6.98-6.89 (m, 2H), 4.59 (t, J=7.2 Hz, 2H), 4.30 (q, J=7.1 Hz, 2H), 3.20 (t, J=7.2 Hz, 2H), 2.68 (s, 3H), 1.34 (t, J=7.1 Hz, 3H); MS (ES+) m/z 361.3 (M+1).

Sources & evidence

ORD record
ord-517c80e9384c4c4f99d71135abd91aec
Source dataset
uspto-grants-2012_09
Patent number
US08258160B2

Reaction notes

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