1-Cyano-4-fluoronaphthalene → HCID 69225857, compound

HRID 916349Notes

Reaction equation

HRID 916349 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]2[NH:12][CH:9]([CH2:10][CH:11]=1)[CH2:8][CH2:7]2)=[O:4].[C:13]([C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18](F)=[CH:17][CH:16]=1)#[N:14]>N1C=CC=CC=1>[CH3:1][O:2][C:3]([C:5]1[CH:6]2[N:12]([C:18]3[C:19]4[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=4)[C:15]([C:13]#[N:14])=[CH:16][CH:17]=3)[CH:9]([CH2:10][CH:11]=1)[CH2:8][CH2:7]2)=[O:4]

Participants

4

Reactant 2

HCID 27367341-Cyano-4-fluoronaphthaleneHCID 69227130HCID 69227130, compound

Product 1

HCID 69225857HCID 69225857, compoundYield 6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

8-Azabicyclo[3.2.1]oct-2-ene-2-carboxylic acid methyl ester (225 mg, 1.35 mmol, Davies H. M. L. et al., J. Org. Chem. 1991, 56, 5696-5700), 1-cyano-4-fluoronaphthalene (230 mg, 1.35 mmol) and pyridine (1.0 mL) were heated to 110° C. for 2 days and concentrated in vacuo. The residue was purified by preparative TLC (ethyl acetate/n-heptane 1:4, 5× eluted) to afford the title compound (25 mg, 6%) as a colorless oil.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by preparative TLC (ethyl acetate/n-heptane 1:4, 5× eluted)

Sources & evidence

ORD record
ord-ccb699591f1743d6826f6863b8ede4c3
Source dataset
uspto-grants-2007_09
Patent number
US07268232B2

Reaction notes

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