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Water → 2-methyl-1-[3-(2-pyridyl)phenyl]-1-(1-trityl-1H-imidazol-4-yl)-1-propanol

HRID 1059232
Notes
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Reaction equation

HRID 1059232 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]([C:13]2[N:14]=[CH:15][N:16]([C:18]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:17]=2)([OH:12])[CH:9]([CH3:11])[CH3:10])[CH:5]=[CH:6][CH:7]=1.C([Sn](CCCC)(CCCC)[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][N:43]=1)CCC.O>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I>[CH3:10][CH:9]([CH3:11])[C:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][N:43]=2)[CH:3]=1)([C:13]1[N:14]=[CH:15][N:16]([C:18]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:17]=1)[OH:12]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 962WaterHCID 6077842-(Tributylstannyl)pyridineHCID 186685221-(3-bromophenyl)-(1-trityl-1H-imidazol-4-yl)-2-methyl-1-propanol

Product 1

HCID 186685632-methyl-1-[3-(2-pyridyl)phenyl]-1-(1-trityl-1H-imidazol-4-yl)-1-propanolYield 51%

Reagents, catalysts & solvents 3

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Catalyst
HCID 178418397HCID 178418397, compoundCatalyst2×
HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

1-(3-Bromophenyl)-(1-trityl-1H-imidazol-4-yl)-2-methyl-1-propanol (1.15 g) and a solution of tri-n-butyl(2-pyridyl)tin (1.01 g) in DMF (10 ml) was deaerated and tetrakis(triphenylphosphine)palladium(0) (73.1 mg) was added. The mixture was stirred under an argon atmosphere at 80° C. for 5 h and copper(I) iodide (20.1 mg) and tetrakis(triphenylphosphine)palladium(0) (48.7 mg) were added. The mixture was stirred at 100° C. for 18 h. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate, washed with 5% aqueous ethylenediamine solution, water (twice) and saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel chomatography (eluent; hexane:ethyl acetate=3:1→2:1). Recrystallization from ethyl acetate-hexane gave the title compound (577 mg, 51%) as colorless powder crystals.

Workup

  1. stirringThe mixture was stirred at 100° C. for 18 h
  2. extractionthe mixture was extracted with ethyl acetate
  3. washwashed with 5% aqueous ethylenediamine solution, water (twice) and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel chomatography (eluent; hexane:ethyl acetate=3:1→2:1)
  7. customRecrystallization from ethyl acetate-hexane

Sources & evidence

ORD record
ord-b223ad18a9ff490e8a4aacc21372dbf8
Source dataset
uspto-grants-2003_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06518257B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes