Toluene → HCID 15658145, compound

HRID 977602Notes

Reaction equation

HRID 977602 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-54f0023f856e4d74aa2161c3818fe7d9
Source dataset
uspto-grants-1997_03
Patent number
US05614634

Reaction notes

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