Methyl iodide → HCID 59425714, compound

HRID 907175Notes

Reaction equation

HRID 907175 reaction equation
[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[C:5]([C:14]#[N:15])=[C:4]1[C:16]1[CH:17]=[CH:18][C:19]2[O:24][CH2:23][C:22](=[O:25])[NH:21][C:20]=2[CH:26]=1)[CH3:2].[H-].[Na+].[CH3:29]I>C1COCC1>[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[C:5]([C:14]#[N:15])=[C:4]1[C:16]1[CH:17]=[CH:18][C:19]2[O:24][CH2:23][C:22](=[O:25])[N:21]([CH3:29])[C:20]=2[CH:26]=1)[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 59425535HCID 59425535, compound

Product 1

HCID 59425714HCID 59425714, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1-Ethyl-6-methoxy-2-(3-oxo-3,4-dihydro-2H-benzo [1,4]oxazin-6-yl)-1H-indole-3-carbonitrile (20 mg, 0.058 mmol), prepared as in example 1BH, was combined with NaH (14 mg, 60% suspension in oil, 0.35 mmol). THF (300 μL) was added. This was stirred at room temperature for 5 minutes. A solution of methyl iodide (4.4 μL) in THF (100 μL) was added. This was stirred at room temperature for 1 hour. The reaction mixture was partitioned between EtOAc and aqueous HCl. The organic layer was dried and concentrated. Purification by silica gel chromatography (9/1, CH2Cl2/EtOAc) yielded 1-ethyl-6-methoxy-2-(4-methyl-3-oxo-3,4,-dihydro-2H-benzo[1,4]oxazin-6-yl)-1H-indole-3-carbonitrile (16 mg, 76%) as a white solid.

Workup

  1. stirringThis was stirred at room temperature for 1 hour
  2. customThe reaction mixture was partitioned between EtOAc and aqueous HCl
  3. customThe organic layer was dried
  4. concentrationconcentrated
  5. customPurification by silica gel chromatography (9/1, CH2Cl2/EtOAc)

Sources & evidence

ORD record
ord-afa4ff74366f41928d46bb9e147d1f3a
Source dataset
uspto-grants-2011_09
Patent number
US08013006B2

Reaction notes

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