Methyl iodide → HCID 59578436, compound

HRID 1897815Notes

Reaction equation

HRID 1897815 reaction equation
[Li][CH2:2][CH2:3][CH2:4][CH3:5].[Li+].CC([N-]C(C)C)C.[Br:14][C:15]1[CH:16]=[N:17][CH:18]=[CH:19][C:20]=1[Cl:21].C1([CH:25]=[N:26][S:27]([CH3:30])(=[O:29])=[O:28])CC1.CI>C1COCC1.O>[Br:14][C:15]1[C:20]([Cl:21])=[C:19]([CH:2]([CH:3]2[CH2:5][CH2:4]2)[N:26]([CH3:25])[S:27]([CH3:30])(=[O:29])=[O:28])[CH:18]=[N:17][CH:16]=1

Participants

8

Reactant 5

HCID 6328Methyl iodideHCID 8176963-Bromo-4-chloropyridineHCID 2724682Lithium diisopropylamideHCID 66788560N-(cyclopropylmethylene)methanesulfonamideHCID 178418339Butyllithium

Product 1

HCID 59578436HCID 59578436, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent4×

Conditions

Temperature
-78 °C

Procedure

To a solution of DIPA (1.71 mL, 12 mmol) in THF (50 mL) at −78° C. was added 1.6M BuLi (7.5 mL, 12.0 mmol) and the mixture was stirred at −78° C. for 2 h. The LDA solution was cannulated into a solution of 3-bromo-4-chloropyridine (2.117 g, 11 mmol) in THF (50 mL) at −78° C., and the mixture was stirred at −78° C. for 1 h. A solution of N-(cyclopropylmethylene)methanesulfonamide (10 mmol, crude mixture) in THF (50 mL) was added and the mixture was stirred at −78° C. for 1 h. A solution of MeI (0.625 mL, 10 mmol) in THF (10 mL) was added, and the mixture was warmed to room temperature and stirred overnight. Water (0.5 mL) was added and the mixture was concentrated in vacuo. The residue was purified by silica gel chromatography eluting with a 0-50% EtOAc-heptane gradient to give N-((5-bromo-4-chloropyridin-3-yl)(cyclopropyl)methyl)-N-methylmethanesulfonamide. MS (ESI): m/z 353.0, 355.0 (M+H)+.

Workup

  1. stirringthe mixture was stirred at −78° C. for 1 h
  2. stirringthe mixture was stirred at −78° C. for 1 h
  3. temperaturethe mixture was warmed to room temperature
  4. stirringstirred overnight
  5. concentrationthe mixture was concentrated in vacuo
  6. customThe residue was purified by silica gel chromatography
  7. washeluting with a 0-50% EtOAc-heptane gradient

Sources & evidence

ORD record
ord-c7c34e6414364064b6bce994936410e9
Source dataset
uspto-grants-2013_08
Patent number
US08519142B2

Reaction notes

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