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 2038727Notes

Reaction equation

HRID 2038727 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-b5dc88c31824455fa053b7f58ecd8d43
Source dataset
uspto-grants-2013_11
Patent number
US08575336B2

Reaction notes

Loading…