Toluene → HCID 19917439, compound

HRID 1756357Notes

Reaction equation

HRID 1756357 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][CH:9]([OH:18])[C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][OH:17])[CH:11]=2)[N:3]=1.[C:19]1([CH3:25])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].[Pd](Cl)Cl>[OH:18][CH:9]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][OH:17])[CH:11]=1)[CH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2](/[CH:4]=[CH:8]/[CH:9]([OH:18])[CH2:10][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:19][CH3:25])[N:3]=1

Participants

4

Reactant 2

HCID 1140TolueneHCID 19966478HCID 19966478, compound

Product 1

HCID 19917439HCID 19917439, compound

Reagents, catalysts & solvents 1

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst

Procedure

Under the conditions of example 24D, 96 mg of 2-bromo-6[(2RS)-2-hydroxy-2-(3-hydroxymethylphenyl)-ethyl]-pyridine and 160 mg of (1E)-1-(tri-n-butylstannyl)-1-undecen-(3RS)-3-ol in 1 ml of toluene is reacted in the presence of 1,1'-bis-(diphenylphosphino)-ferrocene-palladium(II) chloride as catalyst and worked up. The crude product is chromatographed on silica gel with hexane/0-25% ethyl acetate. 20 mg of the title compound is obtained as wine-red oil.

Workup

  1. customThe crude product is chromatographed on silica gel with hexane/0-25% ethyl acetate

Sources & evidence

ORD record
ord-88cc52acafda4254bad7559b973b96dc
Source dataset
uspto-grants-1995_08
Patent number
US05440044

Reaction notes

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