Methyl iodide → HCID 11482971, compound

HRID 749505Notes

Reaction equation

HRID 749505 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-09f171db7230442eb1c7a6acb0426946
Source dataset
uspto-grants-2008_07
Patent number
US07402672B2

Reaction notes

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