2-Bromomethylnaphthalene → HCID 936893, compound

HRID 1033002Notes

Reaction equation

HRID 1033002 reaction equation
N[C:2]1[C:3](SC(C)(C)C)=[N:4][C:5](C)=[C:6](CC)[CH:7]=1.BrC[C:18]1[CH:27]=[CH:26][C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=1.[CH:28]([N:31](C(C)C)CC)(C)C>C(#N)C>[C:21]1([CH2:28][NH:31][C:3]2[CH:2]=[CH:7][CH:6]=[CH:5][N:4]=2)[C:20]2[C:25](=[CH:26][CH:27]=[CH:18][CH:19]=2)[CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 703202-BromomethylnaphthaleneHCID 81531DiisopropylethylamineHCID 10105052HCID 10105052, compound

Product 1

HCID 936893HCID 936893, compoundYield 62.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 3-amino-2-tert-butylthio-5-ethyl-6-methylpyridine (0.15 g, 0.67 mmol), 2-bromomethyl-napthalene (0.15 g, 0.67 mmol), diisopropylethylamine (86 mg, 0.67 mmol) in acetonitrile (5 mL) was refluxed under an atmosphere of nitrogen for 16 hours. The resultant mixture was concentrated under reduced pressure (15 (torr). The residue was subjected to column chromatography on silica gel (50, elution with 1% methanol in chloroform). Collection and concentration of appropriate fractions provided 98 mg (40%) of the napthylmethylaminopyridine.

Workup

  1. temperaturewas refluxed under an atmosphere of nitrogen for 16 hours
  2. concentrationThe resultant mixture was concentrated under reduced pressure (15 (torr)
  3. customCollection and concentration of appropriate fractions

Sources & evidence

ORD record
ord-8809eb84f1ad4137842a7d6249b0298f
Source dataset
uspto-grants-1994_05
Patent number
US05308854

Reaction notes

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