Boron tribromide → Methyl 4-[(5,6-dichloro-2-{[4-(hydroxy)-phenyl]imino}-3-methyl-2,3-dihydro-1h-benzimidazol-1-yl)methyl]benzoate

HRID 1594522Notes

Reaction equation

[Cl:1][C:2]1[C:31]([Cl:32])=[CH:30][C:5]2[N:6]([CH2:19][C:20]3[CH:29]=[CH:28][C:23]([C:24]([O:26][CH3:27])=[O:25])=[CH:22][CH:21]=3)[C:7](=[N:10][C:11]3[CH:16]=[CH:15][C:14]([O:17]C)=[CH:13][CH:12]=3)[N:8]([CH3:9])[C:4]=2[CH:3]=1.B(Br)(Br)Br>C(Cl)Cl>[Cl:1][C:2]1[C:31]([Cl:32])=[CH:30][C:5]2[N:6]([CH2:19][C:20]3[CH:29]=[CH:28][C:23]([C:24]([O:26][CH3:27])=[O:25])=[CH:22][CH:21]=3)[C:7](=[N:10][C:11]3[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=3)[N:8]([CH3:9])[C:4]=2[CH:3]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To the title compound of Example 19 Step C (0.11 mmol, 50 mg) in CH2Cl2 (0.5 mL) cooled to −78° C. was added dropwise BBr3 (0.33 mol, 330 μL of a 1 M solution in CH2Cl2). After addition, the reaction was removed from the cold bath for 30 min, then cooled to −78° C. and diluted with MeOH. The mixture was concentrated under reduced pressure and the product was isolated by chromatography on silica eluting with 4% MeOH in CH2Cl2 as a white solid. LC-MS (ESI, Method B): 1.80 min, m/z 456.1 (M+1).

Workup

additionAfter addition
customthe reaction was removed from the cold bath for 30 min
additiondiluted with MeOH
concentrationThe mixture was concentrated under reduced pressure
customthe product was isolated by chromatography on silica eluting with 4% MeOH in CH2Cl2 as a white solid
custom1.80 min, m/z 456.1 (M+1)

Sources & evidence

ORD record: ord-0ed1f94ebad9404ca693e12e11583ad4
Source dataset: uspto-grants-2007_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07301036B2

Reaction notes

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