ChemicalBook CAS DataBase List tert-butyl N-[(6-cyanopyridin-3- yl)Methyl]carbaMate

tert-butyl N-[(6-cyanopyridin-3- yl)Methyl]carbaMate synthesis

12synthesis methods

Product Name:tert-butyl N-[(6-cyanopyridin-3- yl)Methyl]carbaMate
CAS Number:302341-61-3
Molecular formula:C12H15N3O2
Molecular Weight:233.27

557-21-1 Synthesis

557-21-1
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TERT-BUTYL [(6-CHLOROPYRIDIN-3-YL)METHYL]CARBAMATE

285119-72-4
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$60.00/25mg

tert-butyl N-[(6-cyanopyridin-3-
yl)Methyl]carbaMate

302341-61-3
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Yield:302341-61-3 90%

Reaction Conditions:

1,1'-bis-(diphenylphosphino)ferrocene;tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ in N,N-dimethyl-formamide at 70;

Steps:

55

Preparation 55; 5-Aminomethyl-2-(piperidin-l-ylmethyl)-pyridine; S-ffert-Butoxycarbonylamino-methvD--cyano-pyridine; Under a nitrogen atmosphere, add 3-(tert-butoxycarbonylamino-methyl)-6-chloropyridine (13.1 g, 54 mmol), zinc cyanide (9.5 g, 81 mmol), tris(dibenzylideneacetone)dipalladium(0) (494 mg, 0.54 mmol), and dppf (550 mg, 0.81 mmol) to DMF (130 mL). Heat the mixture at 70⁰C overnight. Cool the mixture to room temperature and dilute with water and EtOAc, Separate the layers, and extract the aqueous layer with EtOAc. Wash the combined organic extracts with water and brine. Dry the organic solution over Na₂SO₄, filter, and concentrate in vacuo. Purify by chromatography on silica gel (500 g) eluting with hexane/EtOAc (1 :0 to 7:3 gradient) to provide the desired intermediate as a white solid (11.3 g, 90%). MS (ES+) m/z: 234 (M+H)⁺.

References:

WO2007/28083,2007,A2 Location in patent:Page/Page column 103-104