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

HRID 526827
Notes
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Reaction equation

HRID 526827 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 5735921-methyl-1H-imidazole-5-carbaldehydeHCID 867160576-Bromo-2,4-dichloro-3-phenylquinoline2×HCID 178418339Butyllithium

Product 1

HCID 118006175(2,4-Dichloro-3-phenylquinolin-6-yl)(1-methyl-1H-imidazol-5-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

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

  1. customto quench
  2. additionThe mixture was diluted with water
  3. extractionwas extracted three times with EtOAc
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. 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

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes