Methyl iodide → HCID 11392341, compound

HRID 749504Notes

Reaction equation

HRID 749504 reaction equation
CI.[CH3:3][NH:4][C:5]([C:7]1[NH:15][C:14]2[C:9](=[N:10][CH:11]=[CH:12][CH:13]=2)[C:8]=1[S:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:6].[C:23]([O-])([O-])=O.[Cs+].[Cs+]>N1C=CC=CC=1>[CH3:3][NH:4][C:5]([C:7]1[N:15]([CH3:23])[C:14]2[C:9](=[N:10][CH:11]=[CH:12][CH:13]=2)[C:8]=1[S:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:6]

Participants

5

Reactant 3

HCID 6328Methyl iodide2×HCID 10796Cesium carbonateHCID 11196840HCID 11196840, compound

Product 1

HCID 11392341HCID 11392341, compoundYield 20.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Add methyl iodide (20 mg, 0.164 mmol) at r.t. to a mixture of 3-phenylsulfanyl-1H-pyrrolo[3,2-b]pyridine-2-carboxylic acid methylamide (Ia-33, 47 mg, 0.166 mmol), Cs2CO3 (65 mg, 0.2 mmol) and pyridine (1.5 mL). Heat the reaction at 60° C. in a sealed vessel for 3 hrs. Add additional methyl iodide (20 mg) and moniter the progress on the reaction by chromatography. When complete, cool the mixture, concentrate to dryness and extract into ethyl acetate from brine. Separate the organic phase and concentrate. Purify the residue by flash chromatography twice (SiO2, 3 gm, elute with MeOH 0-4% in DCM; and SiO2, 1 gm, elute with heptane:DCM, 1:1) to provide title compound (10 mg) as a white solid, 1H NMR (CDCl3) and LC-MS (m/e=297) were consistent for the title compound structure.

Workup

  1. temperatureHeat
  2. customthe reaction at 60° C. in a sealed vessel for 3 hrs
  3. customon the reaction by chromatography
  4. temperatureWhen complete, cool the mixture
  5. concentrationconcentrate to dryness
  6. extractionextract into ethyl acetate from brine
  7. customSeparate the organic phase
  8. concentrationconcentrate
  9. customPurify the residue
  10. washby flash chromatography twice (SiO2, 3 gm, elute with MeOH 0-4% in DCM; and SiO2, 1 gm, elute with heptane:DCM, 1:1)

Sources & evidence

ORD record
ord-dbf75f068a3e452389bad163e7cc66c2
Source dataset
uspto-grants-2008_07
Patent number
US07402672B2

Reaction notes

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