4-Fluorobenzyl bromide → ethyl 5-(1-(2-cyclopropylethyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-3-methylthiophene-2-carboxylate

HRID 560803Notes

Reaction equation

HRID 560803 reaction equation
FC1C=CC(CBr)=CC=1.CC1C=CC(S(O[CH2:21][CH2:22][CH:23]2[CH2:25][CH2:24]2)(=O)=O)=CC=1.[CH3:26][C:27]1[CH:31]=[C:30]([N:32]2[C:36](=[O:37])[NH:35][N:34]=[CH:33]2)[S:29][C:28]=1[C:38]([O:40][CH2:41][CH3:42])=[O:39]>>[CH:23]1([CH2:22][CH2:21][N:35]2[C:36](=[O:37])[N:32]([C:30]3[S:29][C:28]([C:38]([O:40][CH2:41][CH3:42])=[O:39])=[C:27]([CH3:26])[CH:31]=3)[CH:33]=[N:34]2)[CH2:24][CH2:25]1

Participants

4

Reactant 3

HCID 680214-Fluorobenzyl bromideHCID 13568392Toluene-4-sulfonic acid 2-cyclopropyl-ethyl esterHCID 59481255ethyl 3-methyl-5-(5-oxo-1H-1,2,4-triazol-4(5H)-yl)thiophene-2-carboxylate

Product 1

HCID 58031435ethyl 5-(1-(2-cyclopropylethyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-3-methylthiophene-2-carboxylateYield 80%

Procedure

Following the procedure as described in Example 29, making variations as required to replace 4-fluorobenzyl bromide with 2-cyclopropylethyl 4-methylbenzenesulfonate 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 80% yield: 1H NMR (300 MHz, CDCl3) δ 7.74 (s, 1H), 6.94 (s, 1H), 4.32 (q, J=7.1 Hz, 2H), 2.54 (s, 3H), 3.94 (t, J=7.1 Hz, 2H), 1.72-1.63 (m, 2H), 1.36 (t, J=7.1 Hz, 3H), 0.77-0.63 (m, 1H), 0.49-0.41 (m, 2H), 0.08-0.01 (m, 2H); MS (ES+) m/z 322.3 (M+1).

Sources & evidence

ORD record
ord-36ee64d0727e44559832a3438dfa855f
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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