Methyl iodide → Methyl-(2-methyl-3,4,5,6-tetrahydro-2H-[1,4']bipyridinyl-3'-yl)-carbamic acid tert-butyl ester
Reaction equation
[C:1]([O:5][C:6](=[O:21])[NH:7][C:8]1[CH:9]=[N:10][CH:11]=[CH:12][C:13]=1[N:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH:15]1[CH3:20])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].I[CH3:25].[NH4+].[Cl-]>C1COCC1>[C:1]([O:5][C:6](=[O:21])[N:7]([CH3:25])[C:8]1[CH:9]=[N:10][CH:11]=[CH:12][C:13]=1[N:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH:15]1[CH3:20])([CH3:4])([CH3:2])[CH3:3]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
(2-Methyl-3,4,5,6-tetrahydro-2H[1,4′]bipyridinyl-3′-yl)-carbamic acid tert-butyl ester was dissolved in THF (5 mL) and stirred under argon. NaH (24 mg, 0.98 mmol) was added and after 10 min, iodomethane (61 μL, 0.98 mmol) was added. After stirring for 3 hours, NaH (12 mg, 0.49 mmol) and iodomethane (30 μL, 0.49 mmol) were added again. After 1 h, the reaction mixture was poured into saturated, aqueous NH4Cl solution and extracted three times with EtOAc. The combined organic phases were dried over MgSO4. Filtration followed by removal of volatiles gave crude product. Column chromatography on silica gel (50% EtOAc in n-hexane) gave the desired compound (159 mg, 59% over two steps) that was used in the next step without further purification.
Workup
- stirringAfter stirring for 3 hours
- extractionextracted three times with EtOAc
- dry with materialThe combined organic phases were dried over MgSO4
- filtrationFiltration
- customfollowed by removal of volatiles
- customgave crude product
Sources & evidence
- ORD record
- ord-55ec2f57777e4ecd948f8f74ea41d12d
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08987307B2
Reaction notes
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