Benzene, 1-(chloromethyl)-2-fluoro- → HCID 59490939, compound

HRID 1952223Notes

Reaction equation

HRID 1952223 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:14][C:13]2[C:8](=[N:9][C:10]([CH3:15])=[CH:11][CH:12]=2)[C:7]=1[C:16]1[C:17]([O:22][CH3:23])=[N:18][CH:19]=[CH:20][CH:21]=1)=[O:5])[CH3:2].[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+]>CN(C=O)C.C(OCC)(=O)C.O>[CH2:1]([O:3][C:4]([C:6]1[N:14]([CH2:27][C:26]2[CH:29]=[CH:30][CH:31]=[CH:32][C:25]=2[F:24])[C:13]2[C:8](=[N:9][C:10]([CH3:15])=[CH:11][CH:12]=2)[C:7]=1[C:16]1[C:17]([O:22][CH3:23])=[N:18][CH:19]=[CH:20][CH:21]=1)=[O:5])[CH3:2]

Participants

7

Reactant 3

HCID 9580Benzene, 1-(chloromethyl)-2-fluoro-HCID 10796Cesium carbonateHCID 59490898HCID 59490898, compound

Product 1

HCID 59490939HCID 59490939, compoundYield 96.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-(2-Methoxy-pyridin-3-yl)-5-methyl-1H-pyrrolo[3,2-b]pyridine-2-carboxylic acid ethyl ester B3 (0.2 g, 0.64 mmol) was diluted with DMF (4 mL). To the resulting solution was added 2-fluorobenzyl chloride (0.14 g, 0.96 mmol) and cesium carbonate (0.312 g, 0.96 mmol) and the resulting suspension was allowed to stir at room temperature. After 24 hours the reaction mixture was then diluted with ethyl acetate (50 mL) and water (20 mL) 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), dried (magnesium sulfate), filtered and concentrated in vacuo. The crude residue obtained was purified using flash chromatography to provide 1-(2-Fluoro-benzyl)-3-(2-methoxy-pyridin-3-yl)-5-methyl-1H-pyrrolo[3,2-b]pyridine-2-carboxylic acid ethyl ester B4 (0.26 g) MS: 420.20 (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 materialdried (magnesium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude residue obtained
  7. customwas purified

Sources & evidence

ORD record
ord-16e340a66dd64e249f22dbea08998e10
Source dataset
uspto-grants-2013_03
Patent number
US08404845B2

Reaction notes

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