Ammonium Chloride → (2,4-Dichloro-3-phenylquinolin-6-yl)(1-methyl-1H-imidazol-5-yl)methanol

HRID 526827Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([Cl:12])[C:6]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[C:5]2[Cl:19].[CH3:20][N:21]1[C:25]([CH:26]=[O:27])=[CH:24][N:23]=[CH:22]1.[Li]CCCC.[NH4+].[Cl-]>C1COCC1>[Cl:12][C:7]1[C:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:5]([Cl:19])[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([CH:26]([C:25]3[N:21]([CH3:20])[CH:22]=[N:23][CH:24]=3)[OH:27])[CH:3]=2)[N:8]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a cloudy mixture of 6-bromo-2,4-dichloro-3-phenylquinoline (290.5 mg, 0.823 mmol, Intermediate 1: step c) and 1-methyl-1H-imidazole-5-carbaldehyde (90.6 mg, 0.823 mmol) in THF (8 mL) under nitrogen at −78° C. was added n-BuLi (1.6 M in hexane, 0.643 mL, 1.03 mmol) dropwise. The resulting solution was stirred at −78° C. for 3 hours, then was warmed to 0° C. for 15 minutes before addition of saturated aqueous NH4Cl to quench. The mixture was diluted with water and was extracted three times with EtOAc. The organic phase was dried (Na2SO4), filtered, and concentrated. The residue was purified by flash column chromatography (silica gel, 0-6% MeOH-DCM) to afford the title compound as a white powder.

Workup

customto quench
additionThe mixture was diluted with water
extractionwas extracted three times with EtOAc
dry with materialThe organic phase was dried (Na2SO4)
filtrationfiltered
concentrationconcentrated
customThe residue was purified by flash column chromatography (silica gel, 0-6% MeOH-DCM)

Sources & evidence

ORD record: ord-398e13f5c3e6453ea8f346ebcbc5804d
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346782B2

Reaction notes

Loading…