Boron tribromide → 5-Ethyl-2-fluoro-4-[3-(1,4,5,6,7,8-hexahydro-imidazo[4,5-d]azepin-2-yl)-1H-indazol-6-yl]-phenol trihydrobromide salt

HRID 2038733Notes

Reaction equation

HRID 2038733 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:34][C:28]4[CH2:29][CH2:30][NH:31][CH2:32][CH2:33][C:27]=4[N:26]=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:34][C:28]5[CH2:29][CH2:30][NH:31][CH2:32][CH2:33][C:27]=5[N:26]=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 tribromideHCID 1363339752-[6-(2-ethyl-5-fluoro-4-methoxy-phenyl)-1H-indazol-3-yl]-1,4,5,6,7,8-hexahydro-imidazo[4,5-d]azepine

Product 1

HCID 1363339625-Ethyl-2-fluoro-4-[3-(1,4,5,6,7,8-hexahydro-imidazo[4,5-d]azepin-2-yl)-1H-indazol-6-yl]-phenol trihydrobromide saltYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 1M solution of boron tribromide in DCM (3.18 mL, 3.18 mmol) was added dropwise to a solution of 2-[6-(2-ethyl-5-fluoro-4-methoxy-phenyl)-1H-indazol-3-yl]-1,4,5,6,7,8-hexahydro-imidazo[4,5-d]azepine (Preparation 31, 410 mg, 796 μmol) in DCM (10 mL) at 0° C. The resulting solution was stirred at room temperature for 18 hours. The precipitated solid was collected by filtration, washed with tBME, then triturated with EtOAc to yield the title compound (380 mg) in a 75% yield.

Workup

  1. filtrationThe precipitated solid was collected by filtration
  2. washwashed with tBME
  3. customtriturated with EtOAc

Sources & evidence

ORD record
ord-f63f6496bd374a11b0a58e4d5923c8eb
Source dataset
uspto-grants-2013_11
Patent number
US08575336B2

Reaction notes

Loading…