Acetic Acid → 7-chloro-1-methyl-1H-pyrrolo[2,3-c]pyridine

HRID 1711037Notes

Reaction equation

HRID 1711037 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[CH:10]=[CH:9][NH:8][C:7]=12.[H-].[Na+].CI.[C:15](O)(=O)C>CN(C=O)C>[Cl:1][C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[CH:10]=[CH:9][N:8]([CH3:15])[C:7]=12

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 114350487-Chloro-1H-pyrrolo[2,3-c]pyridine

Product 1

HCID 594244767-chloro-1-methyl-1H-pyrrolo[2,3-c]pyridineYield 92%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 259 (250 mg, 1.64 mmol) in DMF (16 mL) at 0° C. was added NaH (197 mg, 4.92 mmol, 60% in mineral oil), and the mixture was stirred for 30 min, followed by addition of MeI (112 □L, 1.80 mmol). The reaction mixture was stirred at room temperature for 2 h before acetic acid (1 mL) was added. Solvents were removed under reduced pressure, the residue was partitioned between water and EtOAc. Organic phase was collected, dried over anhydrous Na2SO4 and concentrated. The residue was purified by flash column chromatography, eluent EtOAc/hexane (1:1), to afford the title compound 263 (200 mg, 92% yield) as an off-white solid. MS (m/z): 167.1 (M+H) (found).

Workup

  1. additionwas added
  2. customSolvents were removed under reduced pressure
  3. customthe residue was partitioned between water and EtOAc
  4. customOrganic phase was collected
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified by flash column chromatography, eluent EtOAc/hexane (1:1)

Sources & evidence

ORD record
ord-865abc7761884e8dbd96128d27840337
Source dataset
uspto-grants-2010_09
Patent number
US07790729B2

Reaction notes

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