Methyl iodide → HCID 51037313, compound

HRID 1045818Notes

Reaction equation

HRID 1045818 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]([NH:10][C:11]2[CH:12]=[N:13][CH:14]=[N:15][CH:16]=2)[CH:7]=[N:8][CH:9]=1.[CH3:17]I>C1COCC1.CCOC(C)=O>[Br:3][C:4]1[CH:5]=[C:6]([N:10]([CH3:17])[C:11]2[CH:16]=[N:15][CH:14]=[N:13][CH:12]=2)[CH:7]=[N:8][CH:9]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 58349171HCID 58349171, compound

Product 1

HCID 51037313HCID 51037313, compoundYield 143.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

NaH (17 mg, 0.71 mmol, 1.1 eq) was added to a flame-dried round-bottom flask and anhydrous THF (1.2 mL) was added. The slurry was cooled to 0° C. and compound 10 (164 mg, 0.653 mmol, 1.00 eq) was added as a solution in THF (1.2 mL). After stirring at 0° C. for 30 minutes methyl iodide (44.8 μL, 0.708 mmol, 1.10 eq) was added and the reaction was allowed to warm to room temperature while stirring overnight. The reaction was diluted with EtOAc and washed with water (1×). The aqueous layer was back extracted (1×) with EtOAc and the combined organics were washed with brine, dried (MgSO4), filtered and concentrated in vacuo. Purification by flash chromatography on silica gel afforded 248 mg (93%) of the title compound as a tan solid: 1H NMR (400 MHz, CDCl3) δ 8.84 (s, 1H), 8.62 (s, 2H), 8.35 (d, J=2.4 Hz, 1H), 8.30 (d, J=1.9 Hz, 1H), 7.78 (t, J=2.2 Hz, 1H), 3.36 (s, 3H); [M+1]+: 265.0.

Workup

  1. additionwas added
  2. temperatureto warm to room temperature
  3. washwashed with water (1×)
  4. extractionThe aqueous layer was back extracted (1×) with EtOAc
  5. washthe combined organics were washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customPurification by flash chromatography on silica gel

Sources & evidence

ORD record
ord-83f544a2673a4ef3999d7db84bd6c349
Source dataset
uspto-grants-2013_10
Patent number
US08569308B2

Reaction notes

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