Ethyl Acetate → HCID 59490911, compound

HRID 1952227Notes

Reaction equation

HRID 1952227 reaction equation
[CH3:1][O:2][C:3]([C:5]1[NH:15][C:8]2=[CH:9][N:10]=[C:11]([O:13][CH3:14])[CH:12]=[C:7]2[C:6]=1[C:16]1[C:17]([O:22][CH3:23])=[N:18][CH:19]=[CH:20][CH:21]=1)=[O:4].[F:24][C:25]1[CH:32]=[CH:31][CH:30]=[CH:29][C:26]=1[CH2:27]Cl.C(=O)([O-])[O-].[Cs+].[Cs+].C(OCC)(=O)C>CN(C=O)C.O>[CH3:1][O:2][C:3]([C:5]1[N:15]([CH2:27][C:26]2[CH:29]=[CH:30][CH:31]=[CH:32][C:25]=2[F:24])[C:8]2=[CH:9][N:10]=[C:11]([O:13][CH3:14])[CH:12]=[C:7]2[C:6]=1[C:16]1[C:17]([O:22][CH3:23])=[N:18][CH:19]=[CH:20][CH:21]=1)=[O:4]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 9580Benzene, 1-(chloromethyl)-2-fluoro-HCID 10796Cesium carbonateHCID 59490907HCID 59490907, compound

Product 1

HCID 59490911HCID 59490911, compoundYield 75.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

5-methoxy-3-(2-methoxy-pyridin-3-yl)-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid methyl ester C4 (0.07 g, 0.22 mmol) was diluted with DMF (2 mL) and to the resulting solution was added 2-fluorobenzyl chloride (0.048 g, 0.33 mmol) and cesium carbonate (0.107 g, 0.33 mmol). The resulting suspension was allowed to stir at room temperature for 24 hours, then ethyl acetate (50 mL) and water (20 mL) were added to the reaction mixture and the layers were separated. The organic layer was sequentially washed with aqueous saturated sodium bicarbonate solution (10 mL), water (10 mL) and saturated brine (10 mL). The combined organic layers were dried (magnesium sulfate), filtered and concentrated in vacuo to provide a crude residue which was purified using flash chromatography to provide 1-(2-Fluoro-benzyl)-5-methoxy-3-(2-methoxy-pyridin-3-yl)-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid methyl ester C5 (0.07 g, 75%) MS: 422.20 (M+H)+.

Workup

  1. customthe layers were separated
  2. washThe organic layer was sequentially washed with aqueous saturated sodium bicarbonate solution (10 mL), water (10 mL) and saturated brine (10 mL)
  3. dry with materialThe combined organic layers were dried (magnesium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto provide a crude residue which
  7. customwas purified

Sources & evidence

ORD record
ord-94d5f5c3e14145a6bc7d714d52fa4253
Source dataset
uspto-grants-2013_03
Patent number
US08404845B2

Reaction notes

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