4-Fluorobenzyl bromide → ethyl 3-methyl-5-(1-(4-(methylsulfonyl)benzyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)thiophene-2-carboxylate

HRID 560805Notes

Reaction equation

HRID 560805 reaction equation
FC1C=CC(CBr)=CC=1.[CH3:10][S:11]([C:14]1[CH:21]=[CH:20][C:17]([CH2:18]Br)=[CH:16][CH:15]=1)(=[O:13])=[O:12].[CH3:22][C:23]1[CH:27]=[C:26]([N:28]2[C:32](=[O:33])[NH:31][N:30]=[CH:29]2)[S:25][C:24]=1[C:34]([O:36][CH2:37][CH3:38])=[O:35]>>[CH3:22][C:23]1[CH:27]=[C:26]([N:28]2[C:32](=[O:33])[N:31]([CH2:18][C:17]3[CH:20]=[CH:21][C:14]([S:11]([CH3:10])(=[O:13])=[O:12])=[CH:15][CH:16]=3)[N:30]=[CH:29]2)[S:25][C:24]=1[C:34]([O:36][CH2:37][CH3:38])=[O:35]

Participants

4

Reactant 3

HCID 680214-Fluorobenzyl bromideHCID 27335814-(Methylsulfonyl)benzyl BromideHCID 59481255ethyl 3-methyl-5-(5-oxo-1H-1,2,4-triazol-4(5H)-yl)thiophene-2-carboxylate

Product 1

HCID 58031651ethyl 3-methyl-5-(1-(4-(methylsulfonyl)benzyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)thiophene-2-carboxylateYield 81%

Procedure

Following the procedure as described in Example 29, making variations as required to replace 4-fluorobenzyl bromide with 4-methylsulfonylbenzyl 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 81% yield: 1H NMR (300 MHz, CDCl3) δ 7.94 (d, J=7.9 Hz, 2H), 7.76 (s, 1H), 7.59 (d, J=7.9 Hz, 2H), 6.95 (s, 1H), 5.10 (s, 2H), 4.32 (q, J=7.1 Hz, 2H), 3.04 (s, 3H), 2.55 (s, 3H), 1.36 (t, J=7.1 Hz, 3H); MS (ES+) m/z 444.3 (M+23).

Sources & evidence

ORD record
ord-e74ec31e0930487ba2a8aa5519b75cee
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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