Tetrahydrofuran → 4-bromo-1-(4'-methyl-[1,1'-biphenyl]-4-yl)-1H-pyrazole

HRID 923629Notes

Reaction equation

HRID 923629 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH:18]=[CH:17][CH:16]=[N:15]3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C1C(=O)N([Br:26])C(=O)C1.C1COCC1>C(Cl)Cl>[Br:26][C:17]1[CH:16]=[N:15][N:14]([C:11]2[CH:12]=[CH:13][C:8]([C:5]3[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=3)=[CH:9][CH:10]=2)[CH:18]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 67184N-bromobutanimideHCID 710783191-(4'-methyl-[1,1'-biphenyl]-4-yl)-1H-pyrazole

Product 1

HCID 710784354-bromo-1-(4'-methyl-[1,1'-biphenyl]-4-yl)-1H-pyrazoleYield 87.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Prepared from INT-85: To a stirring solution of 1-(4′-methyl-[1,1′-biphenyl]-4-yl)-1H-pyrazole (309 mg, 1.319 mmol) INT-85 in DCM (4 mL) was added NBS (258 mg, 1.45 mmol). After stirring at room temperature for 1 h additional THF (4 mL) was added and stirring continued. After 18 h the reaction mixture was concentrated in vacuo and slurried in MeCN (4 mL). The solid was collected by filtration and washed with MeCN (2×2 mL) to provide 360 mg (87%) of 4-bromo-1-(4′-methyl-[1,1′-biphenyl]-4-yl)-1H-pyrazole INT-86. LCMS-ESI (m/z) calculated for C16H13BrN2: 312; found 313 [M+H]+, tR=3.07 min (Method 5).

Workup

  1. customPrepared from INT-85
  2. additionwas added
  3. concentrationAfter 18 h the reaction mixture was concentrated in vacuo
  4. filtrationThe solid was collected by filtration
  5. washwashed with MeCN (2×2 mL)

Sources & evidence

ORD record
ord-341fc3b7e3294f849c909fb4ea015f6a
Source dataset
uspto-grants-2016_03
Patent number
US09278910B2

Reaction notes

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