Toluene → HCID 15658145, compound

HRID 1756354Notes

Reaction equation

HRID 1756354 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][CH:9]([OH:21])[C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([O:18][CH2:19]C)=[O:17])[CH:11]=2)[N:3]=1.[C:22]1([CH3:28])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=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:21][CH:9]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([O:18][CH3:19])=[O:17])[CH:11]=1)[CH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2](/[CH:4]=[CH:8]/[CH:9]([OH:21])[CH2:10][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:22][CH3:28])[N:3]=1

Participants

4

Reactant 2

HCID 1140TolueneHCID 19966479HCID 19966479, compound

Product 1

HCID 15658145HCID 15658145, compound

Reagents, catalysts & solvents 1

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

Conditions

Temperature
100 °C

Procedure

A solution of 120 mg of 2-bromo-6-[(2RS)-2-hydroxy-2-(3-ethoxycarbonylphenyl)-ethyl]-pyridine in 0.7 ml of toluene is mixed with 180 mg of (1E)-1-(tri-n-butylstannyl)-1-undecen-(3RS)-3-ol and 22 mg of 1,1'-bis-(diphenylphosphino)-ferrocene-palladium(II) chloride and stirred under argon atmosphere for 2 hours at 100° C. The reaction mixture is evaporated to dryness and the residue is chromatographed on silica gel with hexane/0-15% ethyl acetate. 56 mg of the title compound is obtained as oil.

Workup

  1. customThe reaction mixture is evaporated to dryness
  2. customthe residue is chromatographed on silica gel with hexane/0-15% ethyl acetate

Sources & evidence

ORD record
ord-5407d88f578b467d99f1f077fc6fcdde
Source dataset
uspto-grants-1995_08
Patent number
US05440044

Reaction notes

Loading…