Methyl iodide → HCID 10089418, compound

HRID 273104Notes

Reaction equation

HRID 273104 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]([C:11]2[O:15][N:14]=[C:13]([CH2:16][S:17][C:18]3[NH:19][C:20]4[C:21]([N:26]=3)=[N:22][CH:23]=[CH:24][CH:25]=4)[N:12]=2)[CH:8]=[CH:9][CH:10]=1.[CH3:27]I>C1COCC1>[CH3:3][O:4][C:5]1[CH:6]=[C:7]([C:11]2[O:15][N:14]=[C:13]([CH2:16][S:17][C:18]3[N:19]([CH3:27])[C:20]4[C:21]([N:26]=3)=[N:22][CH:23]=[CH:24][CH:25]=4)[N:12]=2)[CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 10449854HCID 10449854, compound

Product 1

HCID 10089418HCID 10089418, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
1 °C

Procedure

THF (3 ml) was added to a mixture of sodium hydride (60%, 8 mg, 0.2 mmol) and 2-[5-(3-methoxy-phenyl)-[1,2,4]oxadiazol-3-ylmethylsulfanyl]-1H-imidazo[4,5-b]pyridine (24.6 mg, 0.072 mmol) and the resulting mixture was stirred at 1° C. for about 15 min. Methyl iodide (20 μL, 0.32 mmol) was added the resulting mixture was stirred at 0° C. for 2 h. The reaction was quenched by the addition of dichloromethane (10 ml) and water (2 ml). After vigorous stirring, the organic extracts (10 ml, plus 3×5 ml) were eluted through a Chem Elut Extraction Column (Varian, cat #1219-8002). Purification using SPE chromatography (5 g silica) using 25/25/50 to 50/25/25 ethyl acetate/dichloromethane/hexane yielded two products. The first product to elute was 2-{1-[5-(3-methoxy-phenyl)-[1,2,4]oxadiazol-3-yl]-ethylsulfanyl}-1-methyl-1H-imidazo[4,5-b]pyridine (6 mg, 23%). 1H NMR (CDCl3), δ (ppm): 8.46 (d, 1H), 7.72 (d, 1H), 7.62 (d, 1H), 7.55 (d, 1H), 7.42 (t, 1H), (m, 2H), 5.67 (q, 1H), 3.88 (s, 3H), 3.71 (s, 3H), 2.01 (d, 3H).

Workup

  1. stirringwas stirred at 0° C. for 2 h
  2. customThe reaction was quenched by the addition of dichloromethane (10 ml) and water (2 ml)
  3. washAfter vigorous stirring, the organic extracts (10 ml, plus 3×5 ml) were eluted through a Chem Elut Extraction Column (Varian, cat #1219-8002)
  4. customPurification
  5. customyielded two products
  6. washThe first product to elute

Sources & evidence

ORD record
ord-4f2d28030243427ebf71c3366bccbe15
Source dataset
uspto-grants-2008_11
Patent number
US07456200B2

Reaction notes

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