N-bromobutanimide → HCID 73294359, compound

HRID 1398051Notes

Reaction equation

HRID 1398051 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[O:19][CH3:20])[N:11]=[C:10]([CH:21]3[CH2:26][C:25]([CH3:28])([CH3:27])[O:24][C:23]([CH3:30])([CH3:29])[CH2:22]3)[CH:9]=2)=[CH:4][CH:3]=1.C1C(=O)N([Br:38])C(=O)C1>C(Cl)Cl>[Br:38][C:9]1[C:10]([CH:21]2[CH2:26][C:25]([CH3:28])([CH3:27])[O:24][C:23]([CH3:30])([CH3:29])[CH2:22]2)=[N:11][N:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[O:19][CH3:20])[C:8]=1[C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 73292924HCID 73292924, compound

Product 1

HCID 73294359HCID 73294359, compoundYield 41.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-(4-chlorophenyl)-1-(2-methoxyphenyl)-3-(2,2,6,6-tetramethyltetrahydro-2H-pyran-4-yl)-1H-pyrazole (80 mg, 0.19 mmol)(Example 1) in 2 mL of DCM was added NBS (33 mg, 0.19 mmol) and the mixture stirred for 30 mins at Rt. The crude product was purified by silica gel chromatography (Thomson Scientific 12-g cartridge, 2-20% EtOAc/heptane) to give 40 mg (40%) of the title compound.

Workup

  1. customThe crude product was purified by silica gel chromatography (Thomson Scientific 12-g cartridge, 2-20% EtOAc/heptane)

Sources & evidence

ORD record
ord-4f190ef0f442479fa84dcb2cc370eb87
Source dataset
uspto-grants-2014_12
Patent number
US08901314B2

Reaction notes

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