Methyl iodide → HCID 58882923, compound

HRID 445710Notes

Reaction equation

HRID 445710 reaction equation
[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[C:9]([CH3:15])=[N:10][CH:11]=[C:12]([Br:14])[CH:13]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].I[CH3:20]>CN(C=O)C>[C:1]([O:5][C:6](=[O:16])[N:7]([C:8]1[C:9]([CH3:15])=[N:10][CH:11]=[C:12]([Br:14])[CH:13]=1)[CH3:20])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 58882943HCID 58882943, compound

Product 1

HCID 58882923HCID 58882923, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A solution of (5-bromo-2-methyl-pyridin-3-yl)-carbamic acid tert-butyl ester (Stage 158.1.2, 4.53 mmol) in DMF (20 ml) was cooled with an ice-bath and 55% NaH in oil (5.89 mmol) was added. The RM was stirred for 25 min at 0° C. then was added iodomethane (5.22 mmol). The RM was stirred for 2 h at it then was quenched with aqueous NaHCO3 and extracted with EtOAc. The organic layer was washed with water (3×), with brine (3×), dried over Na2SO4, filtered, evaporated and dried under vacuum to give the title compound as a brown solid (HPLC: tR 3.20 min (Method A); M+H=301, 303 MS-ES).

Workup

  1. stirringThe RM was stirred for 2 h at it
  2. customthen was quenched with aqueous NaHCO3
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with water (3×), with brine (3×)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customdried under vacuum

Sources & evidence

ORD record
ord-1565fe74eb00417a99f2502ce414a4d2
Source dataset
uspto-grants-2013_07
Patent number
US08476294B2

Reaction notes

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