Methyl iodide → HCID 67209277, compound

HRID 402501Notes

Reaction equation

HRID 402501 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[N:10]=[C:9]2[NH:11][CH:12]=[C:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:8]2=[C:7]([C:20]([F:23])([F:22])[F:21])[CH:6]=1.[CH3:24]I.[NH4+].[Cl-]>CN(C=O)C>[CH3:3][O:4][C:5]1[N:10]=[C:9]2[N:11]([CH3:24])[CH:12]=[C:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:8]2=[C:7]([C:20]([F:23])([F:21])[F:22])[CH:6]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 67209396HCID 67209396, compound

Product 1

HCID 67209277HCID 67209277, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NaH (15 mg, 0.38 mmol) was added to a stirred solution of 6-methoxy-3-phenyl-4-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridine (73 mg, 0.25 mmol) in DMF (3 ml) and the resulting mixture was stirred for 30 min. Then methyl iodide (0.06 ml, 0.99 mmol) was added and the mixture was stirred for additional 1 h. To the mixture saturated aqueous NH4Cl solution was added and the solution was extracted with EtOAc. The organic layer was washed with water and brine, filtered and dried over anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure. The crude product was purified by flash column chromatography (2% EtOAc in hexane) to yield the title compound (72 mg, 94%). [LCMS RtC=0.93 min; [M+H]+=307.0]

Workup

  1. stirringthe mixture was stirred for additional 1 h
  2. extractionthe solution was extracted with EtOAc
  3. washThe organic layer was washed with water and brine
  4. filtrationfiltered
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationThe organic layer was concentrated under reduced pressure
  7. customThe crude product was purified by flash column chromatography (2% EtOAc in hexane)

Sources & evidence

ORD record
ord-578508d6919f46c69a5c1b7a673d0145
Source dataset
uspto-grants-2014_06
Patent number
US08742106B2

Reaction notes

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