Methyl iodide → HCID 59565476, compound

HRID 1962866Notes

Reaction equation

HRID 1962866 reaction equation
[C:1]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([CH:12]=1)=[CH:10][C:9]([O:13][CH:14]([S:25][CH3:26])[C:15]([NH:17][C:18]([CH2:22][O:23][CH3:24])([CH3:21])[CH2:19][OH:20])=[O:16])=[CH:8][C:7]=2[CH3:27])#[CH:2].I[CH3:29].[H-].[Na+]>C1COCC1>[C:1]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([CH:12]=1)=[CH:10][C:9]([O:13][CH:14]([S:25][CH3:26])[C:15]([NH:17][C:18]([CH2:19][O:20][CH3:29])([CH3:21])[CH2:22][O:23][CH3:24])=[O:16])=[CH:8][C:7]=2[CH3:27])#[CH:2]

Participants

5

Reactant 3

HCID 6328Methyl iodide2×HCID 24758Sodium hydrideHCID 595653242-(3-ethynyl-8-methyl-quinolin-6-yloxy)-N-(2-hydroxy-1-methoxymethyl-1-methyl-ethyl)-2-methylsulfanyl-acetamide

Product 1

HCID 59565476HCID 59565476, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(3-ethynyl-8-methyl-quinolin-6-yloxy)-N-(2-hydroxy-1-methoxymethyl-1-methyl-ethyl)-2-methylsulfanyl-acetamide (120 mg) in dry THF (7 ml) NaH (19 mg, 60% in oil) was added at room temperature under a nitrogen atmosphere. After 30 minute iodomethane (30 □l) was added to the reaction mixture. After stirring during 5 h one equivalent of NaH and one equivalent of iodomethane were added. The mixture was stirred overnight at room temperature, then quenched with water and diluted with ethyl acetate. The water phase was extracted twice with ethyl acetate and the combined organic phases dried over sodium sulfate, filtered and evaporated. The crude residue was purified by column chromatography (cyclohexane/ethyl acetate/dichloromethane, 1:1:1) to give 2-(3-ethynyl-8-methyl-quinolin-6-yloxy)-N-(2-methoxy-1-methoxymethyl-1-methyl-ethyl)-2-methylsulfanyl-acetamide (46 mg) as a light brown oil.

Workup

  1. additionwere added
  2. customquenched with water
  3. additiondiluted with ethyl acetate
  4. extractionThe water phase was extracted twice with ethyl acetate
  5. dry with materialthe combined organic phases dried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe crude residue was purified by column chromatography (cyclohexane/ethyl acetate/dichloromethane, 1:1:1)

Sources & evidence

ORD record
ord-767ca56a3b754e5f8c7483c1ad898d40
Source dataset
uspto-grants-2013_04
Patent number
US08415272B2

Reaction notes

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