tert-butyl N-[(6-cyanopyridin-3- yl)Methyl]carbaMate synthesis
- 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
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![TERT-BUTYL [(6-CHLOROPYRIDIN-3-YL)METHYL]CARBAMATE](/CAS/GIF/285119-72-4.gif)
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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
181130-13-2
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24424-99-5
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![tert-butyl N-[(6-carbaMoylpyridin-3-
yl)Methyl]carbaMate](/CAS/GIF/800412-55-9.gif)
800412-55-9
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302341-61-3
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67515-95-1
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302341-61-3
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100-54-9
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