Water → HCID 18668634, compound

HRID 1059168Notes

Reaction equation

HRID 1059168 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.[S:37]1[CH:41]=[CH:40][C:39](B(O)O)=[CH:38]1.C(=O)([O-])[O-].[Na+].[Na+].O>C1(C)C(CCO)=CC=CC=1.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>[CH3:10][CH:9]([CH3:11])[C:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([C:39]2[CH:40]=[CH:41][S:37][CH:38]=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]

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 581760Thiophene-3-boronic acidHCID 186685221-(3-bromophenyl)-(1-trityl-1H-imidazol-4-yl)-2-methyl-1-propanol

Product 1

HCID 18668634HCID 18668634, compoundYield 86.5%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 882672-Methylphenethyl alcoholSolvent

Procedure

To a suspension of 1-(3-bromophenyl)-1-(1-trityl-1H-imidazol-4-yl)-2-methyl-1-propanol (1.70 g), 3-thiopheneboronic acid (607 mg) and 2M aqueous sodium carbonate solution (3.16 ml) in toluene-ethanol (6:1) (17.5 ml) was added tetrakis(triphenylphosphine)palladium(0) (110 mg), and the mixture was heated under reflux for 3 h under an argon atmosphere. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate, washed with saturated brine and dried. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chomatography (eluent, hexane:ethyl acetate=6:1→4:1→3:1). Recrystallization from ethyl acetate-hexane gave the title compound (1.48 g) as colorless powder crystals.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 h under an argon atmosphere
  3. extractionthe mixture was extracted with ethyl acetate
  4. washwashed with saturated brine
  5. customdried
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chomatography (eluent, hexane:ethyl acetate=6:1→4:1→3:1)
  8. customRecrystallization from ethyl acetate-hexane

Sources & evidence

ORD record
ord-fb1f5995f67847838e271270ee994ac9
Source dataset
uspto-grants-2003_02
Patent number
US06518257B1

Reaction notes

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