Boron tribromide → 5-Ethyl-2-fluoro-4-[3-(4,5,6,7-tetrahydro-1H-imidazol[4,5-c]pyridin-2-yl)-1H-indazol-6-yl]-phenol trihydrobromide salt

HRID 340075Notes

Reaction equation

HRID 340075 reaction equation
B(Br)(Br)[Br:2].[CH2:5]([C:7]1[CH:12]=[C:11]([O:13]C)[C:10]([F:15])=[CH:9][C:8]=1[C:16]1[CH:24]=[C:23]2[C:19]([C:20]([C:25]3[NH:26][C:27]4[CH2:32][CH2:31][NH:30][CH2:29][C:28]=4[N:33]=3)=[N:21][NH:22]2)=[CH:18][CH:17]=1)[CH3:6]>C(Cl)Cl>[BrH:2].[BrH:2].[BrH:2].[CH2:5]([C:7]1[C:8]([C:16]2[CH:24]=[C:23]3[C:19]([C:20]([C:25]4[NH:26][C:27]5[CH2:32][CH2:31][NH:30][CH2:29][C:28]=5[N:33]=4)=[N:21][NH:22]3)=[CH:18][CH:17]=2)=[CH:9][C:10]([F:15])=[C:11]([OH:13])[CH:12]=1)[CH3:6]

Participants

4

Reactant 2

HCID 25134Boron tribromide2×HCID 178436890HCID 178436890, compound

Product 1

HCID 1784192405-Ethyl-2-fluoro-4-[3-(4,5,6,7-tetrahydro-1H-imidazol[4,5-c]pyridin-2-yl)-1H-indazol-6-yl]-phenol trihydrobromide saltYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 1M solution of boron tribromide in DCM (4.54 mL, 4.54 mmol) was added dropwise to a solution of 2-[6-(2-ethyl-5-fluoro-4-methoxy-phenyl)-1H-indazol-3-yl]-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine (Preparation 24, 739 mg, 1.13 mmol) in DCM (10 mL) at 0° C. The resulting solution was stirred at room temperature for 18 hours. Further boron tribromide (4.54 mL, 4.54 mmol) was added dropwise and the reaction was allowed to stir at room temperature for 5 hours. Precipitated solid was collected by filtration, washed with tBME, then triturated with EtOAc to yield the title compound as the trihydrobromide salt (665 mg) in a 94% yield.

Workup

  1. stirringto stir at room temperature for 5 hours
  2. customPrecipitated solid
  3. filtrationwas collected by filtration
  4. washwashed with tBME
  5. customtriturated with EtOAc

Sources & evidence

ORD record
ord-e7f62e3c2bcf4579a1c4ed4f886c1844
Source dataset
uspto-grants-2014_11
Patent number
US08895544B2

Reaction notes

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