Toluene → HCID 178435532, compound

HRID 1368558Notes

Reaction equation

HRID 1368558 reaction equation
BrC1C=C2C(=CC=1)[CH:8]=[C:7]([C:12]([C:17]1[N:18]=[CH:19][N:20](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:21]=1)([OH:16])[CH:13]([CH3:15])[CH3:14])[CH:6]=[CH:5]2.[CH2:41](C([Sn])=C(CCCC)CCCC)CCC.[C:56]1([CH3:62])[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=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>[CH2:62]([C:56]1[CH:61]=[C:60]2[C:59](=[CH:58][CH:57]=1)[CH:8]=[C:7]([C:12]([C:17]1[N:18]=[CH:19][NH:20][CH:21]=1)([OH:16])[CH:13]([CH3:15])[CH3:14])[CH:6]=[CH:5]2)[CH3:41]

Participants

5

Reactant 3

HCID 1140TolueneHCID 22018349HCID 22018349, compoundHCID 53438229Tri(butyl)vinyltin

Product 1

HCID 178435532HCID 178435532, compound

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

A solution of 1-(6-bromonaphthalen-2-yl)-2-methyl-1-(1-trityl-1H-imidazol-4-yl)-1-propanol (2.0 g), tetrakis(triphenylphosphine)palladium (116 mg) and tributylvinyltin (1.40 ml) in toluene (30 ml) was refluxed under argon atmosphere for 80 min. The solvent was distilled off and the residue was purified by column chromatography (eluent, hexane:THF=2:1),then crystallized from isopropyl ether-hexane (1:1) to give the titled compound (1.47 g) as a colorless powder.

Workup

  1. distillationThe solvent was distilled off
  2. customthe residue was purified by column chromatography (eluent, hexane
  3. customTHF=2:1),then crystallized from isopropyl ether-hexane (1:1)

Sources & evidence

ORD record
ord-9f165b7ede0e476da5876cebb700d18a
Source dataset
uspto-grants-2003_06
Patent number
US06573289B1

Reaction notes

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