Boron tribromide → HCID 178450640, compound

HRID 230026Notes

Reaction equation

[C:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([N:11]([C:28]2[N:32]([CH3:33])[C:31]3[CH:34]=[CH:35][C:36]([O:38]C)=[CH:37][C:30]=3[N:29]=2)[CH:12]2[C:20]3[C:15](=[CH:16][C:17]([C:21]([O:23][CH2:24][CH2:25][CH2:26][CH3:27])=[O:22])=[CH:18][CH:19]=3)[CH2:14][CH2:13]2)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].B(Br)(Br)Br>ClCCl>[C:1]([C@H:5]1[CH2:6][CH2:7][C@H:8]([N:11]([C:28]2[N:32]([CH3:33])[C:31]3[CH:34]=[CH:35][C:36]([OH:38])=[CH:37][C:30]=3[N:29]=2)[CH:12]2[C:20]3[C:15](=[CH:16][C:17]([C:21]([O:23][CH2:24][CH2:25][CH2:26][CH3:27])=[O:22])=[CH:18][CH:19]=3)[CH2:14][CH2:13]2)[CH2:9][CH2:10]1)([CH3:2])([CH3:3])[CH3:4]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of butyl 1-[(trans-4-tert-butylcyclohexyl)(5-methoxy-1-methyl-1H-benzimidazol-2-yl)amino]indane-5-carboxylate (0.40 g, 0.75 mmol) in 20 mL of anhydrous dichloromethane at −78° C. was slowly added BBr3 (1.0 M solution in CH2Cl2, 3.8 mL, 3.8 mmol) over 10 min. The reaction mixture was stirred at −78° C. for 30 min and then the cold bath was removed. The reaction was quenched after 20 min with saturated aqueous NaHCO3 (20 mL) and extracted with EtOAc (3×15 mL). The organic layers were combined, dried over Na2SO4 and concentrated. Chromatography afforded butyl 1-[(trans-4-tert-butylcyclohexyl)(5-hydroxy-1-methyl-1H-benzimidazol-2-yl)amino]indane-5-carboxylate. HPLC/MS: m/z=518.4 (M+1), Rt=2.45 min.

Workup

customat −78° C.
customover 10 min
customthe cold bath was removed
customThe reaction was quenched after 20 min with saturated aqueous NaHCO3 (20 mL)
extractionextracted with EtOAc (3×15 mL)
dry with materialdried over Na2SO4
concentrationconcentrated

Sources & evidence

ORD record: ord-47a724f3679143659abb1877f8a0a10e
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07563815B2

Reaction notes

Loading…