Methyl iodide → HCID 25015017, compound

HRID 501058Notes

Reaction equation

HRID 501058 reaction equation
[C:1]([O:5][C:6](=[O:26])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[O:15][C:16]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][C:17]=3[CH:18]=2)=[C:10]([F:25])[N:9]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:29]I>CN(C=O)C>[C:1]([O:5][C:6](=[O:26])[N:7]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[O:15][C:16]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][C:17]=3[CH:18]=2)=[C:10]([F:25])[N:9]=1)[CH3:29])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6328Methyl iodide2×HCID 24758Sodium hydride2×HCID 25015018HCID 25015018, compound

Product 1

HCID 25015017HCID 25015017, compoundYield 81.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of [6-fluoro-5-(5-methoxy-benzofuran-2-yl)-pyridin-2-yl]-carbamic acid tert-butyl ester (78 mg, 0.218 mmol) in DMF (5 mL) at 0° C., NaH (11 mg, 0.26 mmol, 57% dispersion in oil) was added and the resulting mixture was stirred for 10 minutes. Methyl iodide (15 μL, 0.24 mmol) was then added and the stirring was continued for 30 minutes at room temperature. Additional portions of NaH (11 mg, 0.26 mmol, 57% dispersion in oil) and methyl iodide (15 μL, 0.24 mmol) were added and the solution was stirred for 1 hour. The reaction mixture was quenched with water (5 mL) and the product was extracted with ethyl acetate. The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated. Purification of the crude product by flash column chromatography using 10% ethyl acetate in hexane afforded title compound (66 mg) as an off-white solid. 1H NMR (400 MHz, CHLOROFORM-d) δ: 8.25-8.33 (m, 1 H) 7.87 (m 1H) 7.41 (d, J=9.37 Hz, 1 H) 7.14 (s, 1 H) 7.06 (d, J=2.34 Hz, 1 H) 6.92 (d, J=8.98 Hz, 1 H) 3.86 (s, 3 H) 3.43 (s, 3 H) 1.56 (s, 9 H)

Workup

  1. waitthe stirring was continued for 30 minutes at room temperature
  2. stirringthe solution was stirred for 1 hour
  3. customThe reaction mixture was quenched with water (5 mL)
  4. extractionthe product was extracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification of the crude product by flash column chromatography

Sources & evidence

ORD record
ord-4a3531f4a32548c59dc0734acec6ef81
Source dataset
uspto-grants-2010_08
Patent number
US07772256B2

Reaction notes

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