Methyl iodide → HCID 11482971, compound

HRID 1865183Notes

Reaction equation

HRID 1865183 reaction equation
CI.[C:3]1([S:9][C:10]2[C:14]3=[N:15][CH:16]=[CH:17][CH:18]=[C:13]3[NH:12][C:11]=2[C:19]([NH2:21])=[O:20])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:22]([O-])([O-])=O.[Cs+].[Cs+]>N1C=CC=CC=1>[CH3:22][N:12]1[C:13]2[C:14](=[N:15][CH:16]=[CH:17][CH:18]=2)[C:10]([S:9][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)=[C:11]1[C:19]([NH2:21])=[O:20]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 11482594HCID 11482594, compound

Product 1

HCID 11482971HCID 11482971, compoundYield 38.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Add methyl iodide (20 mg, 0.14 mmol) at r.t. to a mixture of 3-phenylsulfanyl-1H-pyrrolo[3,2-b]pyridine-2-carboxylic acid amide (Ia-1, 27 mg, 0.1 mmol), Cs2CO3 (43 mg, 0.13 mmol) in pyridine (0.5 ml). Heat the reaction at 80° C. in a sealed vessel for 15 minutes. Cool the mixture cooled and extract into ethyl acetate from water. Separate the organic solution and evaporate. Purify the residue (33 mg) by flash chromatography (silica gel, 3 gm, elute with MeOH 0-4% in dichloromethane) to provide the title compound (11 mg) as a white solid, 1H NMR (CDCl3) and LC-MS (m/e=283) are consistent for the title compound structure.

Workup

  1. temperatureHeat
  2. customthe reaction at 80° C. in a sealed vessel for 15 minutes
  3. temperatureCool the mixture
  4. temperaturecooled
  5. extractionextract into ethyl acetate from water
  6. customSeparate the organic solution
  7. customevaporate
  8. customPurify the residue (33 mg)
  9. washby flash chromatography (silica gel, 3 gm, elute with MeOH 0-4% in dichloromethane)

Sources & evidence

ORD record
ord-dc83a7e47a6249279fcf923d637d3290
Source dataset
uspto-grants-2009_12
Patent number
US07626027B2

Reaction notes

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