Methyl iodide → HCID 11998050, compound

HRID 908580Notes

Reaction equation

HRID 908580 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:10][N:9]=[C:8]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)[N:7]=1.[CH3:17][Si](C)(C)[N-][Si](C)(C)C.[Na+].IC>C1COCC1>[CH3:17][N:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:10][N:9]=[C:8]([C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)[N:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 135428707HCID 135428707, compound

Product 1

HCID 11998050HCID 11998050, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

3-{5-(1H-pyrrol-2-yl)-[1,2,4]oxadiazol-3-yl}-pyridine (1 g; 0.5 mmol) in 15 ml of dry THF at −70° C. was added 0.18 g of sodium hexamethyl disilazide (1 mmol), the reaction mixture was stirred at −70° C. for 30 min. and at 0° C. for 1 hour. The reaction mixture was cooled to −70° C. and added 0.076 g of iodomethane (0.52 mmol). The reaction mixture was stirred at −70° C. for ½ hour, then at room temperature overnight. The product was isolated by column chromatography. Yield 0.04 g of yellow solid (37%). Mp. 108-109° C.

Workup

  1. temperatureThe reaction mixture was cooled to −70° C.
  2. stirringThe reaction mixture was stirred at −70° C. for ½ hour
  3. customat room temperature
  4. customovernight
  5. customThe product was isolated by column chromatography

Sources & evidence

ORD record
ord-0068ef21f88a4e0ba77db360fafaa032
Source dataset
uspto-grants-2011_09
Patent number
US08017631B2

Reaction notes

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