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

HRID 2392162Notes

Reaction equation

HRID 2392162 reaction equation
C1C(=O)N([Br:8])C(=O)C1.[CH3:9][N:10]1[C:14]([C:15]2[CH:16]=[C:17]([C:20]([O:22][CH3:23])=[O:21])[S:18][CH:19]=2)=[CH:13][CH:12]=[N:11]1>O1CCCC1>[Br:8][C:13]1[CH:12]=[N:11][N:10]([CH3:9])[C:14]=1[C:15]1[CH:16]=[C:17]([C:20]([O:22][CH3:23])=[O:21])[S:18][CH:19]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 57826540Methyl 4-(1-methyl-1H-pyrazol-5-yl)thiophene-2-carboxylate

Product 1

HCID 57826395methyl 4-(4-bromo-1-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxylateYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

NBS (747 mg, 4.20 mmol) was added in portions to a 50 mL sealed tube reactor containing methyl 4-(1-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxylate (860 mg, 3.48 mmol) [prepared according to the procedure of Example 37] in Tetrahydrofuran (THF) (17 mL) at room temperature. The mixture was heated to 70° C. for 1.5 hours, cooled to room temperature and partitioned between CHCl3 and H2O. The organic layer was dried with Na2SO4, adsorbed onto silica and purified via column chromatography (20-40% EtOAc/hexanes) affording the title compound (867 mg, 83%): LC-MS (ES) m/z=303 (M+H)+.

Workup

  1. customsealed tube reactor
  2. customprepared
  3. customat room temperature
  4. temperaturecooled to room temperature
  5. custompartitioned between CHCl3 and H2O
  6. dry with materialThe organic layer was dried with Na2SO4
  7. custompurified via column chromatography (20-40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-b8c9532f03b04ec3ac6c1d5c4294e300
Source dataset
uspto-grants-2012_09
Patent number
US08273782B2

Reaction notes

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