Methyl iodide → HCID 90010262, compound

HRID 1056615Notes

Reaction equation

HRID 1056615 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:10](=O)[C:11]([CH3:18])([CH3:17])[C:12]([O:14]CC)=[O:13])[CH:5]=[N:6][C:7]=1[CH2:8][CH3:9].[H-].[Na+].BrC1C=C(C(=O)CC(OCC)=O)C=[N:27]C=1CC.IC>CN(C=O)C.O.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([C:10]2[C:11]([CH3:18])([CH3:17])[C:12](=[O:13])[O:14][N:27]=2)[CH:5]=[N:6][C:7]=1[CH2:8][CH3:9]

Participants

8

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 90010023HCID 90010023, compoundHCID 90010124HCID 90010124, compound

Product 1

HCID 90010262HCID 90010262, compoundYield 54%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Step-2: Ethyl 3-(5-bromo-6-ethylpyridin-3-yl)-2,2-dimethyl-3-oxopropanoate: To a 0° C. cooled and stirred suspension of sodium hydride (60% dispersion inoil, 120 mg, 5 mmol), in DMF (3 mL) was added ethyl 3-(5-bromo-6-ethylpyridin-3-yl)-3-oxopropanoate (0.5 g, 1.66 mmol) in DMF (7 mL) over a period of 15 min. The reaction mixture was then stirred for 15 min at the same temperature and Iodomethane (365 μl, 5.83 mmol) was added to the above mixture. The resulting mixture was then warmed to room temperature and stirred for 3 h. The reaction mixture was diluted with water (30 mL) followed by ethyl acetate (50 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (2×30 mL). The combined organic layers were washed with brine (20 mL), dried (Na2SO4) and filtered. The filtrate was rotary evaporated to afford 300 mg (54%) of the title compound as white solid. 1HNMR (400 MHz, DMSO-d6) δ 8.77 (d, J=2.0 Hz, 1H), 8.18 (d, J=2.0 Hz, 1H), 4.12 (q, J=7.0 Hz, 2H), 2.96 (q, J=7.0 Hz, 2H), 1.46 (s, 6H), 1.25 (t, J=7.0 Hz, 3H), 1.03 (t, J=7.0 Hz, 3H); ESI-MS (m/z) 328, 330 [(MH+, Br79,81].

Workup

  1. additionwas added to the above mixture
  2. stirringstirred for 3 h
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with ethyl acetate (2×30 mL)
  5. washThe combined organic layers were washed with brine (20 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customThe filtrate was rotary evaporated

Sources & evidence

ORD record
ord-64098e4252704159b18e3ca9acbdabb8
Source dataset
uspto-grants-2016_07
Patent number
US09399638B2

Reaction notes

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