Methyl iodide → HCID 117700140, compound

HRID 2205281Notes

Reaction equation

HRID 2205281 reaction equation
[CH2:1]([Li])CCC.[C:6]([NH:10][C:11]([C:13]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][N:14]=1)=[O:12])([CH3:9])([CH3:8])[CH3:7].IC.[NH4+].[Cl-]>C1COCC1>[C:6]([NH:10][C:11]([C:13]1[C:18]([CH3:1])=[C:17]([Cl:19])[CH:16]=[CH:15][N:14]=1)=[O:12])([CH3:9])([CH3:7])[CH3:8]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 24850887N-tert-Butyl-4-chloropyridine-2-carboxamideHCID 178418339Butyllithium

Product 1

HCID 117700140HCID 117700140, compoundYield 76.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

n-Butyllithium (2.5 M in hexanes, 29 mL, 72 mmol) is added dropwise to N-tert-butyl-4-chloropyridine-2-carboxamide (7.00 g, 32.9 mmol) in THF (70 mL) at −78° C. After 1 h at −78° C. iodomethane (6.8 mL, 109 mmol) is added and stirring is continued for 1 h. Saturated NH4Cl (10 mL) is added and the organic layer is separated, dried and evaporated under reduce pressure to give a residue that is purified by flash chromatography (eluent 0-20% EtOAc/cyclohexane) to furnish N-tert-butyl-4-chloro-3-methyl-pyridine-2-carboxamide (5.7 g, 76%).

Workup

  1. customthe organic layer is separated
  2. customdried
  3. customevaporated
  4. customto give a residue that
  5. customis purified by flash chromatography (eluent 0-20% EtOAc/cyclohexane)

Sources & evidence

ORD record
ord-de17cc7b91404cdbb53c4b565cab7da0
Source dataset
uspto-grants-2016_06
Patent number
US09371282B2

Reaction notes

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