Methyl iodide → HCID 22253421, compound

HRID 1612381Notes

Reaction equation

HRID 1612381 reaction equation
Br[C:2]1[C:3]2[N:21]([CH:22]([CH2:25][CH3:26])[CH2:23][CH3:24])[N:20]=[N:19][C:4]=2[C:5]([O:9][C:10]2[C:15]([CH3:16])=[CH:14][C:13]([CH3:17])=[CH:12][C:11]=2[CH3:18])=[N:6][C:7]=1[CH3:8].[Li][CH2:28]CCC.CCCCCC.CI>C1COCC1>[CH2:23]([CH:22]([N:21]1[C:3]2[C:2]([CH3:28])=[C:7]([CH3:8])[N:6]=[C:5]([O:9][C:10]3[C:15]([CH3:16])=[CH:14][C:13]([CH3:17])=[CH:12][C:11]=3[CH3:18])[C:4]=2[N:19]=[N:20]1)[CH2:25][CH3:26])[CH3:24]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8058HexaneHCID 22253402HCID 22253402, compoundHCID 178418339Butyllithium

Product 1

HCID 22253421HCID 22253421, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a −78° C. solution of 7-bromo-1-(1-ethyl-propyl)-6-methyl-4-(2,4,6-trimethyl-phenoxy)-1H-[1,2,3]triazolo[4,5-c]pyridine (33 mg, 0.079 mmol) in 2 ml of dry THF was added 2.5 M nBuLi in hexane (0.047 ml, 0.019 mmol) and stirred at that temperature for 5 min. An excess of MeI (0.5 ml) was added and the mixture was stirred at that temperature for 15 min, then gradually warmed to room temperature for 1 hour. The mixture was quenched with saturated ammonium chloride and extracted with ethyl acetate. The organic layer was dried and concentrated to give 31 mg of a golden oil. The oil was purified through silica gel column chromatography using 5% ethyl acetate in hexane as eluent to give the title compound as white crystals. Mp 127–129° C.; 1H NMR (CDCl3) δ 6.91 (s,2H), 4.83(m,1H), 2.51(s,3H), 2.38(s,3H), 2.33(s,3H), 2.13(s,6H), 2.3–2.5(m,2H), 1.9–2.2(m,2H), 0.86(t,6H) ppm.

Workup

  1. stirringthe mixture was stirred at that temperature for 15 min
  2. customThe mixture was quenched with saturated ammonium chloride
  3. extractionextracted with ethyl acetate
  4. customThe organic layer was dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a66c340131fc475c9ca9899ad4e9c93e
Source dataset
uspto-grants-2006_01
Patent number
US06992188B1

Reaction notes

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