Benzyl Bromide → ethyl 5-(1-benzyl-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-3-methylthiophene-2-carboxylate

HRID 560802Notes

Reaction equation

HRID 560802 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Br)=[CH:4][CH:3]=1.C(Br)C1C=CC=CC=1.[CH3:18][C:19]1[CH:23]=[C:22]([N:24]2[C:28](=[O:29])[NH:27][N:26]=[CH:25]2)[S:21][C:20]=1[C:30]([O:32][CH2:33][CH3:34])=[O:31]>>[CH2:6]([N:27]1[C:28](=[O:29])[N:24]([C:22]2[S:21][C:20]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[C:19]([CH3:18])[CH:23]=2)[CH:25]=[N:26]1)[C:5]1[CH:8]=[CH:9][CH:2]=[CH:3][CH:4]=1

Participants

4

Reactant 3

HCID 7498Benzyl BromideHCID 680214-Fluorobenzyl bromideHCID 59481255ethyl 3-methyl-5-(5-oxo-1H-1,2,4-triazol-4(5H)-yl)thiophene-2-carboxylate

Product 1

HCID 58031644ethyl 5-(1-benzyl-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-3-methylthiophene-2-carboxylateYield 82%

Procedure

Following the procedure as described in Example 29, making variations as required to replace 4-fluorobenzyl bromide with benzyl bromide to react with ethyl 3-methyl-5-(5-oxo-1H-1,2,4-triazol-4(5H)-yl)thiophene-2-carboxylate, the title compound was obtained as a yellowish solid in 82% yield: 1H NMR (300 MHz, CDCl3) δ 7.72 (s, 1H), 7.43-7.31 (m, 5H), 6.94 (s, 1H), 5.01 (s, 2H), 4.32 (q, J=7.1 Hz, 2H), 2.54 (s, 3H), 1.36 (t, J=7.1 Hz, 3H); MS (ES+) m/z 344.2 (M+1).

Sources & evidence

ORD record
ord-5a37fc83f1494a2184e766ea85a0d6f2
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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