Allyltributylstannane → HCID 68008351, compound

HRID 533158Notes

Reaction equation

HRID 533158 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:10](Cl)=[CH:9][C:8]([CH2:12][O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:7][N:6]=1)=[O:4].[CH2:20]([Sn](CCCC)(CCCC)CCCC)[CH:21]=[CH2:22]>C1(C)C=CC=CC=1.CCOC(C)=O.[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>[CH3:1][O:2][C:3]([C:5]1[C:10]([CH2:22][CH:21]=[CH2:20])=[CH:9][C:8]([CH2:12][O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:7][N:6]=1)=[O:4]

Participants

6

Reactant 2

HCID 90628Allyltributylstannane2×HCID 68008682HCID 68008682, compound

Product 1

HCID 68008351HCID 68008351, compoundYield 84%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalyst2×HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
125 °C

Procedure

Tetrakis (triphenylphosphine) palladium (0) (54 mg, 0.046 mmol) was added to a stirred solution of 3-chloro-5-phenoxymethyl-pyridine-2-carboxylic acid methyl ester (130 mg, 0.47 mmol) and allyltri-n-butyltin (0.25 mL, 0.79 mmol) in degassed toluene (1.5 mL) under nitrogen. The mixture was stirred at 125° C. for 20 h. Then further tetrakis (triphenylphosphine) palladium (0) (54 mg, 0.046 mmol) and allyltri-n-butyltin (0.25 mL, 0.79 mmol) were added and the mixture was stirred at 125° C. for 16 h. The mixture was diluted with EtOAc, filtered through a diatomaceous earth pad. The filtrate was evaporated in vacuo. The crude product was purified by flash column chromatography (silica; EtOAc in DCM 0/100 to 100/0). The desired fractions were collected and the solvents evaporated in vacuo to yield 3-allyl-5-phenoxymethyl-pyridine-2-carboxylic acid methyl ester (111 mg, 84% yield) as a yellow oil.

Workup

  1. stirringthe mixture was stirred at 125° C. for 16 h
  2. filtrationfiltered through a diatomaceous earth pad
  3. customThe filtrate was evaporated in vacuo
  4. customThe crude product was purified by flash column chromatography (silica; EtOAc in DCM 0/100 to 100/0)
  5. customThe desired fractions were collected
  6. customthe solvents evaporated in vacuo

Sources & evidence

ORD record
ord-ca7a032033b94c41b15c226aa41d440f
Source dataset
uspto-grants-2014_10
Patent number
US08853237B2

Reaction notes

Loading…