Sodium hydride → ethyl 1-(2,4-difluorobenzyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylate

HRID 2377048Notes

Reaction equation

HRID 2377048 reaction equation
[NH:1]1[C:5]2=[CH:6][N:7]=[C:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:9]=[C:4]2[CH:3]=[CH:2]1.[H-].[Na+].[F:17][C:18]1[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:19]=1[CH2:20]Br>CN(C=O)C>[F:17][C:18]1[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:19]=1[CH2:20][N:1]1[C:5]2=[CH:6][N:7]=[C:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:9]=[C:4]2[CH:3]=[CH:2]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 902971-(Bromomethyl)-2,4-difluorobenzeneHCID 10702827ethyl 1H-pyrrolo[2,3-c]pyridine-5-carboxylate

Product 1

HCID 21892240ethyl 1-(2,4-difluorobenzyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylateYield 48.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of ethyl 1H-pyrrolo[2,3-c]pyridine-5-carboxylate (0.50 g, 2.63 mmol) in DMF (10 mL) under a nitrogen atmosphere was added sodium hydride (0.087 g, 80% in mineral oil, 2.89 mmol) and 2,4-difluorobenzyl bromide (0.60 g, 2.89 mmol). The resulting mixture was stirred for 16 hours at ambient temperature. It was quenched with water (30 mL), and extracted with ethyl acetate (3×30 mL). The combined organic extracts were washed with water (2×30 mL), dried over sodium sulfate, concentrated in vacuo, and purified by flash chromatography. Elution with hexane/ethyl acetate (1:1) provided the title compound as a light yellow solid (0.40 g, 48% yield). 1H NMR (CD3OD) δ ppm. 8.86 (s, 1H), 8.47 (s, 1H), 7.71 (d, 1H, J=3.2 Hz), 7.31 (dd, 1H, J=6.3 Hz), 6.94-7.05 (m, 2H), 6.79 (d, 1H, J=3.2 Hz), 5.63 (s, 2H), 4.46 (q, 2H, J=7.3 Hz), 1.45 (t, 3H, J=7.3 Hz). LCMS (API-ES, M+H+): 317.0

Workup

  1. customIt was quenched with water (30 mL)
  2. extractionextracted with ethyl acetate (3×30 mL)
  3. washThe combined organic extracts were washed with water (2×30 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. custompurified by flash chromatography
  7. washElution with hexane/ethyl acetate (1:1)

Sources & evidence

ORD record
ord-02a62d860cdd4fd69f90ecad2eed3c53
Source dataset
uspto-grants-2008_12
Patent number
US07468375B2

Reaction notes

Loading…