Water → 6-(4-Chloro-benzylamino)-2-fluoro-nicotinic acid methyl ester

HRID 1024184Notes

Reaction equation

HRID 1024184 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7](F)=[N:6][C:5]=1[F:11].[Cl:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18][NH2:19])=[CH:16][CH:15]=1.O>CN(C)C=O>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([NH:19][CH2:18][C:17]2[CH:20]=[CH:21][C:14]([Cl:13])=[CH:15][CH:16]=2)=[N:6][C:5]=1[F:11]

Participants

5

Reactant 3

HCID 962WaterHCID 660364-ChlorobenzylamineHCID 108449402,6-Difluoro-nicotinic acid methyl ester

Product 1

HCID 595933356-(4-Chloro-benzylamino)-2-fluoro-nicotinic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 2,6-difluoro-nicotinic acid methyl ester (60, 2.00 g, 0.0116 mol) in N,N-dimethylformamide (20.0 mL), under an atmosphere of nitrogen at −40° C., was added p-chlorobenzylamine (61, 2.60 mL, 0.0214 mol). The reaction was stirred at −40° C. to −20° C. for 2 hours, then poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with 25% ethyl acetate in hexane to give compound (62, 2.0 g, 58.7%).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. custompurified by silica gel column chromatography
  6. washeluting with 25% ethyl acetate in hexane
  7. customto give compound (62, 2.0 g, 58.7%)

Sources & evidence

ORD record
ord-90325dca41314e8f800eb29574a3d30c
Source dataset
uspto-grants-2014_05
Patent number
US08722702B2

Reaction notes

Loading…