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

HRID 1845567Notes

Reaction equation

HRID 1845567 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-e58f3135df5b4b0687325dca939f44dc
Source dataset
uspto-grants-2015_02
Patent number
US08946278B2

Reaction notes

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