Methyl iodide → HCID 58337652, compound

HRID 1887456Notes

Reaction equation

HRID 1887456 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:5]=[C:6]([NH:13][C:14]2[CH:15]=[N:16][CH:17]=[N:18][CH:19]=2)[CH:7]=[C:8]([N+:10]([O-:12])=[O:11])[CH:9]=1.[CH3:20]I>C1COCC1.CCOC(C)=O>[F:3][C:4]1[CH:5]=[C:6]([N:13]([CH3:20])[C:14]2[CH:19]=[N:18][CH:17]=[N:16][CH:15]=2)[CH:7]=[C:8]([N+:10]([O-:12])=[O:11])[CH:9]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 58337625HCID 58337625, compound

Product 1

HCID 58337652HCID 58337652, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

NaH (4.5 mg, 0.18 mmol, 1.1 eq) was added to a flame-dried round-bottom flask and anhydrous THF (0.4 mL) was added. The slurry was cooled to 0° C. and compound 30 (40 mg, 0.17 mmol, 1.0 eq) was added as a solution in THF (0.4 mL). After stirring at 0° C. for 30 minutes methyl iodide (12 μL, 0.18 mmol, 1.1 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 13 mg (31%) of the title compound as a yellow solid: 1H NMR (400 MHz, DMSO-d6) δ 8.99 (s, 1H), 8.79 (s, 2H), 7.58 (dt, J=2.1, 8.5 Hz, 1H), 7.52 (t, J=1.8 Hz, 1H), 7.33 (dt, J=2.3, 11.2 Hz, 1H), 3.42 (s, 3H); ES-MS [M+1]+: 249.1.

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-6cecbdf443504234ac7987dd7ce48e42
Source dataset
uspto-grants-2013_08
Patent number
US08501757B2

Reaction notes

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