Methyl iodide → 2-(5-chloro-3-pyridyloxy)-N-methyl-N-(2-methylpent-3-yn-2-yl)butyramide

HRID 1374893Notes

Reaction equation

HRID 1374893 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([O:8][CH:9]([CH2:19][CH3:20])[C:10]([NH:12][C:13]([CH3:18])([C:15]#[C:16][CH3:17])[CH3:14])=[O:11])[CH:5]=[N:6][CH:7]=1.[H-].[Na+].[CH3:23]I>O1CCCC1.O>[Cl:1][C:2]1[CH:3]=[C:4]([O:8][CH:9]([CH2:19][CH3:20])[C:10]([N:12]([CH3:23])[C:13]([CH3:14])([C:15]#[C:16][CH3:17])[CH3:18])=[O:11])[CH:5]=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 210783862-(5-chloro-3-pyridyloxy)-N-(2-methylpent-3-yn-2-yl)butyramide

Product 1

HCID 210783932-(5-chloro-3-pyridyloxy)-N-methyl-N-(2-methylpent-3-yn-2-yl)butyramide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-(5-chloro-3-pyridyloxy)-N-(2-methylpent-3-yn-2-yl)butyramide (0.10 g; prepared as described in Example 1) in dry tetrahydrofuran (9 ml) was added sodium hydride (0.011 g) at ambient temperature under an atmosphere of nitrogen. The mixture was stirred for 0.75 hours, a solution of methyl iodide (0.023 ml) in dry tetrahydrofuran was added then the reaction mixture stirred for a further 0.5 hours at ambient temperature. The reaction was diluted with water, extracted with ethyl acetate (three times) and the extracts were combined, washed with brine, dried over magnesium sulphate and evaporated under reduced pressure. The residual oil was fractionated by chromatography (silica:hexane/ethyl acetate, 3:1 by volume) to give the required product as a beige solid, 0.075 g. m.p. 67–68° C. 1H NMR (CDCl3) δ: 1.14 (3H, t); 1.68 (3H, s); 1.69 (3H, s); 1.85 (3H, s); 2.02 (2H, m); 3.20 (3H, s); 4.70 (1H, t); 7.18 (1H, m); 8.18 (1H, m); 8.20 (1H, m).

Workup

  1. stirringthe reaction mixture stirred for a further 0.5 hours at ambient temperature
  2. extractionextracted with ethyl acetate (three times)
  3. washwashed with brine
  4. dry with materialdried over magnesium sulphate
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-6beefb51f899460ebf5acbc8a27d731b
Source dataset
uspto-grants-2007_01
Patent number
US07166621B2

Reaction notes

Loading…