N-bromobutanimide → methyl 4-(4-bromo-1-methyl-1H-pyrazol-5-yl)-5-ethyl-2-thiophenecarboxylate

HRID 1961266Notes

Reaction equation

[CH2:1]([C:3]1[S:7][C:6]([C:8]([O:10][CH3:11])=[O:9])=[CH:5][C:4]=1[C:12]1[N:16]([CH3:17])[N:15]=[CH:14][CH:13]=1)[CH3:2].[Br:18]N1C(=O)CCC1=O>O1CCCC1>[Br:18][C:13]1[CH:14]=[N:15][N:16]([CH3:17])[C:12]=1[C:4]1[CH:5]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[S:7][C:3]=1[CH2:1][CH3:2]

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of methyl 5-ethyl-4-(1-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxylate (600 mg, 2.40 mmol) [prepared according to Example 98] in Tetrahydrofuran (THF) (10 ml) was added N-bromosuccinimide (512 mg, 2.88 mmol). The mixture stirred in a sealed tube at 70° C. for 2 h. The reaction mixture was then concentrated and purified with silica gel using a 0-5% gradient (ethyl acetate/hexane) to afford the title compound as an off-white solid: LC-MS (ES) m/z 330 (M+H)+.

Workup

concentrationThe reaction mixture was then concentrated
custompurified with silica gel using a 0-5% gradient (ethyl acetate/hexane)

Sources & evidence

ORD record: ord-9d5f135c74c84acdbd0a81a915416206
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08410158B2

Reaction notes

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