N-bromobutanimide → HCID 59632559, compound

HRID 2369027Notes

Reaction equation

HRID 2369027 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([C:11]2[S:15][C:14]([C:16]3[CH:20]=[CH:19][N:18]([CH3:21])[N:17]=3)=[CH:13][CH:12]=2)[CH:8]=[CH:9][CH:10]=1)(=[O:4])=[O:3].[Br:22]N1C(=O)CCC1=O>C(Cl)Cl>[Br:22][C:20]1[C:16]([C:14]2[S:15][C:11]([C:7]3[CH:8]=[CH:9][CH:10]=[C:5]([S:2]([CH3:1])(=[O:4])=[O:3])[CH:6]=3)=[CH:12][CH:13]=2)=[N:17][N:18]([CH3:21])[CH:19]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimide2×HCID 59631861HCID 59631861, compound

Product 1

HCID 59632559HCID 59632559, compoundYield 79.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3-[5-(3-methanesulfonyl-phenyl)-thiophen-2-yl]-1-methyl-1H-pyrazole (0.10 g, 0.31 mmol) in DCM (3 mL, anhyd) was added N-bromosuccinimide (NBS) (56 mg, 0.31 mmol). After 22 h additional NBS (56 mg) was added and stirring was continued at ambient temperature. After 46 h (total) the reaction mixture was concentrated under reduced pressure and purified by chromatography (silica, EtOAc/Hex, 20:80 to 40:60) to give the title compound (98 mg, 79%) as a white solid. 1H-NMR (CD2Cl2): δ 8.17 (1H, m), 7.91 (1H, m), 7.82 (1H, m), 7.72 (1H, d), 7.61 (1H, m), 7.50 (1H, s), 7.44 (1H, d), 3.91 (3H, s), 3.08 (3H, s).

Workup

  1. customwas continued at ambient temperature
  2. concentrationAfter 46 h (total) the reaction mixture was concentrated under reduced pressure
  3. custompurified by chromatography (silica, EtOAc/Hex, 20:80 to 40:60)

Sources & evidence

ORD record
ord-f21a18a4fefd4819b3096fcb9b7168dc
Source dataset
uspto-grants-2014_04
Patent number
US08703805B2

Reaction notes

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