Methyl iodide → HCID 59424803, compound

HRID 501061Notes

Reaction equation

HRID 501061 reaction equation
[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[C:13]([F:14])=[CH:12][C:11]([Br:15])=[CH:10][N:9]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:19]I>CN(C=O)C>[C:1]([O:5][C:6](=[O:16])[N:7]([C:8]1[C:13]([F:14])=[CH:12][C:11]([Br:15])=[CH:10][N:9]=1)[CH3:19])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 59424793HCID 59424793, compound

Product 1

HCID 59424803HCID 59424803, compoundYield 74.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (5-bromo-3-fluoro-pyridin-2-yl)-carbamic acid tert-butyl ester (600 mg, 2.06 mmol) in dry DMF (20 mL), NaH (130 mg, 3.08 mmol) was added at 0° C. The solution was stirred vigorously for 10 minutes at 0° C. and MeI (180 μL, 2.88 mmol) was added. After 30 minutes, the reaction mixture was quenched with NH4Cl (saturated aqueous solution) and the product was extracted with EtOAc (3×40 mL). The combined organic extracts were washed with water, dried over MgSO4 and concentrated in vacuo. The residue was purified by Biotage using 3-15% EtOAc in hexane to afford title compound (470 mg) as a white solid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 8.23 (d, J=1.95 Hz, 1 H) 7.52 (dd, J=8.59, 1.95 Hz, 1 H) 3.22 (s, 3 H) 1.37 (s, 9 H)

Workup

  1. waitAfter 30 minutes
  2. customthe reaction mixture was quenched with NH4Cl (saturated aqueous solution)
  3. extractionthe product was extracted with EtOAc (3×40 mL)
  4. washThe combined organic extracts were washed with water
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by Biotage

Sources & evidence

ORD record
ord-0b51486539b44455bf2d0c497d074240
Source dataset
uspto-grants-2010_08
Patent number
US07772256B2

Reaction notes

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