Boron tribromide → HCID 73292405, compound

HRID 1398034Notes

Reaction equation

HRID 1398034 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]C)[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.B(Br)(Br)Br>C(Cl)Cl>[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[OH:19])[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

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 73292924HCID 73292924, compound

Product 1

HCID 73292405HCID 73292405, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5-(4-chloro-phenyl)-1-(2-methoxy-phenyl)-3-(2,2,6,6-tetramethyl-tetrahydro-pyran-4-yl)-1H-pyrazole (Example 1) (105 mg, 0.25 mmol) in mL of DCM at −78° C. was added a 1M solution of boron tribromide (0.33 mL, 0.33 mmol) in DCM. After 1 hr at −78° C. the reaction was quenched with 3 mL of 1N HCl and then diluted with 50 mL of EtOAc. The organic layer was washed with 50 mL of NaHCO3 and brine, and dried over Na2SO4. The crude product was purified by silica gel chromatography (Thomson Scientific 12-g cartridge, 2-40% EtOAc in heptane in column volumes) to give 60 mg (59%) of the title compound as a white solid.

Workup

  1. customAfter 1 hr at −78° C. the reaction was quenched with 3 mL of 1N HCl
  2. additiondiluted with 50 mL of EtOAc
  3. washThe organic layer was washed with 50 mL of NaHCO3 and brine
  4. dry with materialdried over Na2SO4
  5. customThe crude product was purified by silica gel chromatography (Thomson Scientific 12-g cartridge, 2-40% EtOAc in heptane in column volumes)

Sources & evidence

ORD record
ord-89cf9e7375fc45bb98ea88b862babcb5
Source dataset
uspto-grants-2014_12
Patent number
US08901314B2

Reaction notes

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