Tributylstannane → 2-Fluoro-4-pyridin-3-ylmethyl-benzonitrile

HRID 1594878Notes

Reaction equation

HRID 1594878 reaction equation
C1(OC(=S)O[CH:10]([C:17]2[CH:22]=[CH:21][C:20]([C:23]#[N:24])=[C:19]([F:25])[CH:18]=2)[C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)C=CC=CC=1.CC(N=NC(C#N)(C)C)(C#N)C.C([SnH](CCCC)CCCC)CCC>C1C=CC=CC=1>[F:25][C:19]1[CH:18]=[C:17]([CH2:10][C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)[CH:22]=[CH:21][C:20]=1[C:23]#[N:24]

Participants

5

Reactant 3

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 88184430thiocarbonic acid O-[(4-cyano-3-fluoro-phenyl)-pyridin-3-yl-methyl]Ester O-phenyl Ester

Product 1

HCID 543806602-Fluoro-4-pyridin-3-ylmethyl-benzonitrile

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of thiocarbonic acid O-[(4-cyano-3-fluoro-phenyl)-pyridin-3-yl-methyl]ester O-phenyl ester (as described in Step A above) (0.5 g, 1.37 mmol) in benzene (2.0 mL) was added AIBN (0.18 g, 1.1 mmol) and tri-n-butyltinhydride (1.09 mL, 4.0 mmol) and the solution was heated to refluxed for 2 hr. The solvents were removed in vacuo to obtain the title compound after chromatography (silica gel, CH2Cl2:MeOH 99:1).

Workup

  1. temperaturethe solution was heated
  2. temperatureto refluxed for 2 hr
  3. customThe solvents were removed in vacuo

Sources & evidence

ORD record
ord-0f4ceab516944c9dbb440c7296c2a865
Source dataset
uspto-grants-2001_09
Patent number
US06284755B1

Reaction notes

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