Lithium Chloride → Ethyl [3-(pyridin-3-yl)phenyl]acetate

HRID 1494059Notes

Reaction equation

HRID 1494059 reaction equation
FC(F)(F)S(O[C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1)(=O)=O.FC(F)(F)S(O[C:21]1[CH:22]=[C:23]([CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH:24]=[CH:25][CH:26]=1)(=O)=O.C[Sn](C)C.C[Sn](C)C.[Cl-].[Li+]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[N:9]1[CH:10]=[CH:11][CH:12]=[C:7]([C:25]2[CH:24]=[C:23]([CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH:22]=[CH:21][CH:26]=2)[CH:8]=1

Participants

6

Reactant 4

HCID 433294Lithium ChlorideHCID 6327618HexamethylditinHCID 110315793-Pyridyl TrifluoromethanesulfonateHCID 14986694HCID 14986694, compound

Product 1

HCID 14986695Ethyl [3-(pyridin-3-yl)phenyl]acetate

Reagents, catalysts & solvents 1

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalyst

Procedure

3-(Trifluoromethylsulfonyloxy)-pyridine is condensed with ethyl m-(trifluoromethanesulfonyloxy)-phenylacetate in the presence of hexamethylditin, lithium chloride and tetrakis-(triphenylphosphine)-palladium to obtain ethyl m-(3-pyridyl)-phenylacetate. The product is alkylated with 1-bromo-4-chlorobutane to obtain the alpha-(4-chlorobutyl)-substituted phenylacetic acid ester. The ester is then reduced to the aldehyde which is condensed with e.g. methyl(triphenylphosphoranylidene)-acetate. The resulting alpha,beta-unsaturated ester is saturated to methyl 8-chloro-4-[m-(3-pyridyl)-phenyl]-octanoate which is converted to methyl 8-amino-4-[m-(3-pyridyl)-phenyl]octanoate according to methodology described herein.

Sources & evidence

ORD record
ord-ba4a6f00648b4884bc9481b41dd9d363
Source dataset
uspto-grants-1991_06
Patent number
US05025025

Reaction notes

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