Benzyl Alcohol → Benzyl 5-(4-methoxyphenyl)-6-methylpyridine-2-carboxylate

HRID 2093174Notes

Reaction equation

HRID 2093174 reaction equation
IC1N=[C:6]([CH3:8])[C:5]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)=CC=1.C([N:19]([CH2:22][CH3:23])[CH2:20][CH3:21])C.[CH2:24]([OH:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[C]=[O:33]>C(#N)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[CH3:16][O:15][C:12]1[CH:11]=[CH:10][C:9]([C:5]2[CH:6]=[CH:8][C:22]([C:23]([O:31][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[O:33])=[N:19][C:20]=2[CH3:21])=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 577048056-Iodo-3-(4-methoxyphenyl)-2-methylpyridineHCID 178418416HCID 178418416, compound

Product 1

HCID 57704814Benzyl 5-(4-methoxyphenyl)-6-methylpyridine-2-carboxylate

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 6342AcetonitrileSolvent

Procedure

6-iodo-3-(4-methoxyphenyl)-2-methylpyridine (100 mg, 0.308 mmol), dichloro bis(triphenylphosphine)palladium(II) (22 mg, 0.031 mmol), triethylamine (46.7 mg, 0.462 mmol), benzyl alcohol (1 mL, 9.66 mmol) were mixed in acetonitrile (3 mL). The resulting mixture was placed under to carbon monoxide at 45 psi at 60° C. for 18 hours. The resulting reaction crude was purified by preparative TLC on SiO2 (eluted with 25% ethyl acetate in hexanes then 10% triethylamine, 20% ethyl acetate in hexanes) to afford benzyl 5-(4-methoxyphenyl)-6-methylpyridine-2-carboxylate. LCMS calc.=333.14; found=334.13 (M+1)+.

Workup

  1. customThe resulting reaction crude
  2. customwas purified by preparative TLC on SiO2 (
  3. washeluted with 25% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-5618b6ced4104feeb00a8a7982281a60
Source dataset
uspto-grants-2013_05
Patent number
US08440702B2

Reaction notes

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