Methyl iodide → 1h-Pyrrolo[2,3-c]pyridine-5-carboxylic acid,1-[(4-fluorophenyl)methyl]-4-methoxy-,methyl ester

HRID 2377086Notes

Reaction equation

HRID 2377086 reaction equation
[F:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][N:7]2[C:11]3=[CH:12][N:13]=[C:14]([C:17]([O:19][CH3:20])=[O:18])[C:15]([OH:16])=[C:10]3[CH:9]=[CH:8]2)=[CH:4][CH:3]=1.[H-].[Na+].I[CH3:26]>CN(C=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:11]3=[CH:12][N:13]=[C:14]([C:17]([O:19][CH3:20])=[O:18])[C:15]([O:16][CH3:26])=[C:10]3[CH:9]=[CH:8]2)=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 53237467methyl 1-(4-fluorobenzyl)-4-hydroxy-1H-pyrrolo[2,3-c]pyridine-5-carboxylate

Product 1

HCID 691970091h-Pyrrolo[2,3-c]pyridine-5-carboxylic acid,1-[(4-fluorophenyl)methyl]-4-methoxy-,methyl esterYield 38.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To methyl 1-(4-fluorobenzyl)-4-hydroxy-1H-pyrrolo[2,3-c]pyridine-5-carboxylate (0.25 g, 0.83 mmol) in DMF (10 mL) were added sodium hydride (0.037 g, 0.92 mmol, 60% in mineral oil) and iodomethane (0.057 mL. 0.92 mmol). The solution was stirred for 3 h at ambient temperature. The reaction mixture was quenched with saturated aqueous ammonium chloride solution (10 mL), and extracted with ethyl acetate (3×50 mL). The organic extracts were washed with brine (3×50 mL), dried over sodium sulfate, concentrated in vacuo and purified by flash chromatography. Elution with ethyl acetate provided the title compound as a solid (0.10 g, 38% yield). 1H NMR (CD3OD) δ: 8.43 (s, 1H), 7.61 (d, 1H, J=3.1 Hz), 7.24 (t, 2H, J=8.8 Hz), 7.05 (t, 2H, J=8.8 Hz), 6.92 (d, 1H, J=3.1 Hz), 5.52 (s, 2H), 4.16 (s, 3H), 3.91 (s, 3H). LCMS (APCI, M+H+): 315.0.

Workup

  1. customThe reaction mixture was quenched with saturated aqueous ammonium chloride solution (10 mL)
  2. extractionextracted with ethyl acetate (3×50 mL)
  3. washThe organic extracts were washed with brine (3×50 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. custompurified by flash chromatography
  7. washElution with ethyl acetate

Sources & evidence

ORD record
ord-3f55fe91725d448b990422d9767cd2be
Source dataset
uspto-grants-2008_12
Patent number
US07468375B2

Reaction notes

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