Boron tribromide → HCID 178419278, compound

HRID 340086Notes

Reaction equation

HRID 340086 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-7e7b9c6d60d94b3f9c179f4dfe0223a3
Source dataset
uspto-grants-2014_11
Patent number
US08895544B2

Reaction notes

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