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Methyl iodide → Methyl-(2-methyl-3,4,5,6-tetrahydro-2H-[1,4']bipyridinyl-3'-yl)-carbamic acid tert-butyl ester

HRID 877986
Notes
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Reaction equation

HRID 877986 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6328Methyl iodide2×HCID 24758Sodium hydride2×HCID 25517Ammonium ChlorideHCID 70663222(2-Methyl-3,4,5,6-tetrahydro-2H-[1,4]bipyridinyl-3'-yl)-carbamic acid tert-butyl ester

Product 1

HCID 70663618Methyl-(2-methyl-3,4,5,6-tetrahydro-2H-[1,4']bipyridinyl-3'-yl)-carbamic acid tert-butyl esterYield 59%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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

  1. stirringAfter stirring for 3 hours
  2. extractionextracted three times with EtOAc
  3. dry with materialThe combined organic phases were dried over MgSO4
  4. filtrationFiltration
  5. customfollowed by removal of volatiles
  6. customgave crude product

Sources & evidence

ORD record
ord-55ec2f57777e4ecd948f8f74ea41d12d
Source dataset
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08987307B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes