Methyl iodide → HCID 67215739, compound

HRID 472927Notes

Reaction equation

HRID 472927 reaction equation
[C:1](=O)([O-])[O-].[Cs+].[Cs+].CI.[NH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([C:18]2[N:22]3[CH:23]=[CH:24][CH:25]=[C:26]([OH:27])[C:21]3=[CH:20][N:19]=2)=[O:17])=[CH:12][C:11]=1[O:28][CH3:29].C(=O)([O-])O.[Na+]>CN(C=O)C>[NH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([C:18]2[N:22]3[CH:23]=[CH:24][CH:25]=[C:26]([O:27][CH3:1])[C:21]3=[CH:20][N:19]=2)=[O:17])=[CH:12][C:11]=1[O:28][CH3:29]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 516892Sodium BicarbonateHCID 11851868HCID 11851868, compound

Product 1

HCID 67215739HCID 67215739, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.79 g (2.43 mmol) of cesium carbonate and then 0.05 ml (0.84 mmol) of methyl iodide are added to 0.22 g (0.76 mmol) of (4-amino-3-methoxyphenyl)(8-hydroxy-imidazo[1,5-a]pyridin-3-yl)methanone obtained in example 147 in 5 ml of DMF. The reaction medium is stirred at ambient temperature for 4 hours. After addition of a saturated sodium hydrogencarbonate solution, the reaction medium is extracted with ethyl acetate. The organic phase obtained is dried over sodium sulfate and concentrated under reduced pressure. The residue is purified by column chromatography on silica gel, elution being carried out with dichloromethane. 0.2 g of an orangy-yellow solid is collected. Melting point: 229° C.; 1H NMR (CDCl3): 3.86 (3H, s), 4.01 (3H, s), 5.80 (2H, m), 6.69 (1H, m), 6.69-6.72 (1H, m), 7.03-7.09 (1H, t), 7.78 (1H, s), 7.92 (1H, s), 8.24 (1H, m), 9.25-9.28 (1H, m)

Workup

  1. extractionthe reaction medium is extracted with ethyl acetate
  2. customThe organic phase obtained
  3. dry with materialis dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is purified by column chromatography on silica gel, elution
  6. custom0.2 g of an orangy-yellow solid is collected

Sources & evidence

ORD record
ord-e0030bce83f942c7bd9fc59fe7799c51
Source dataset
uspto-grants-2014_01
Patent number
US08633216B2

Reaction notes

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