Boron tribromide → HCID 178419278, compound

HRID 2038739Notes

Reaction equation

HRID 2038739 reaction equation
B(Br)(Br)[Br:2].Cl.Cl.Cl.[F:8][C:9]1[C:10]([O:38]C)=[CH:11][C:12]([CH2:33][C:34]([F:37])([F:36])[F:35])=[C:13]([C:15]2[CH:23]=[C:22]3[C:18]([C:19]([C:24]4[NH:32][C:27]5[CH2:28][NH:29][CH2:30][CH2:31][C:26]=5[N:25]=4)=[N:20][NH:21]3)=[CH:17][CH:16]=2)[CH:14]=1>C(Cl)Cl>[BrH:2].[BrH:2].[F:8][C:9]1[CH:14]=[C:13]([C:15]2[CH:23]=[C:22]3[C:18]([C:19]([C:24]4[NH:25][C:26]5[CH2:31][CH2:30][NH:29][CH2:28][C:27]=5[N:32]=4)=[N:20][NH:21]3)=[CH:17][CH:16]=2)[C:12]([CH2:33][C:34]([F:35])([F:36])[F:37])=[CH:11][C:10]=1[OH:38]

Participants

4

Reactant 2

HCID 25134Boron tribromide2×HCID 1363339762-{6-[5-Fluoro-4-methoxy-2-(2,2,2-trifluoro-ethyl)-phenyl]-1H-indazol-3-yl}-4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridine trihydrochloride salt

Product 1

HCID 178419278HCID 178419278, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boron tribromide (750 μL, 7.83 mmol) was added driowuse to a solution of 2-{6-[5-fluoro-4-methoxy-2-(2,2,2-trifluoro-ethyl)-phenyl]-1H-indazol-3-yl}-4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridine trihydrochloride salt (Preparation 38, 2.03 g, 3.66 mmol) in DCM (25 mL) at 0° C. The resulting solution was stirred at room temperature for 18 hours. Further boron tribromide (2 mL, 20.7 mmol) was added dropwise and the reaction mixture was allowed to stir at room temperature for 18 hours. The precipitated solid was collected by filtration, washed with DCM and triturated with EtOAc to yield the title compound as the dihydrobromide salt (1.56 g) in a 67% yield.

Workup

  1. stirringto stir at room temperature for 18 hours
  2. filtrationThe precipitated solid was collected by filtration
  3. washwashed with DCM
  4. customtriturated with EtOAc

Sources & evidence

ORD record
ord-a932459b03dc4f2d9103fcd8e91d2325
Source dataset
uspto-grants-2013_11
Patent number
US08575336B2

Reaction notes

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