Acetic Acid → [5-(2-Ethylaminomethyl-4-fluoro-phenyl)-pyridin-3-yl]-acetic acid ethyl ester

HRID 554637Notes

Reaction equation

HRID 554637 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[CH2:5][C:6]1[CH:7]=[N:8][CH:9]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=2[CH:19]=O)[CH:11]=1)[CH3:2].C([BH3-])#N.[Na+].[CH2:26]([NH2:28])[CH3:27].C(O)(=O)C>CO>[CH2:1]([O:3][C:4](=[O:21])[CH2:5][C:6]1[CH:7]=[N:8][CH:9]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=2[CH2:19][NH:28][CH2:26][CH3:27])[CH:11]=1)[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6341EthylamineHCID 5003444Sodium cyanoborohydrideHCID 58565095[5-(4-Fluoro-2-formyl-phenyl)-pyridin-3-yl]-acetic acid ethyl ester

Product 1

HCID 58565094[5-(2-Ethylaminomethyl-4-fluoro-phenyl)-pyridin-3-yl]-acetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To [5-(4-fluoro-2-formyl-phenyl)-pyridin-3-yl]-acetic acid ethyl ester (1.2 g, 4.18 mmol) in MeOH was added sodium cyanoborohydride (0.394 g, 6.26 mmol) and ethylamine (2M in THF; 3.13 mL, 6.26 mmol). Acetic acid (0.36 mL, 6.26 mmol) was added, and the reaction was stirred for 2 hours at room temperature. The mixture was concentrated, and the residue was dissolved in CH2Cl2 and washed with saturated aqueous NaHCO3 and H2O. The organic layer was dried over Na2SO4, filtered, and concentrated, and the residue was purified by silica gel chromatography (0-10% MeOH in CH2Cl2) to give [5-(2-ethylaminomethyl-4-fluoro-phenyl)-pyridin-3-yl]-acetic acid ethyl ester.

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutionthe residue was dissolved in CH2Cl2
  3. washwashed with saturated aqueous NaHCO3 and H2O
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customthe residue was purified by silica gel chromatography (0-10% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-bcfea68e130e4e5fa38015084e661147
Source dataset
uspto-grants-2011_11
Patent number
US08049015B2

Reaction notes

Loading…