Acetic Acid → Ethyl 3-(5-(2-(((4-bromo-2-fluorophenyl)amino)methyl)-5-chlorophenyl)picolinamido)propanoate

HRID 405131Notes

Reaction equation

HRID 405131 reaction equation
[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[Cl:15][C:16]1[CH:17]=[CH:18][C:19]([CH:38]=O)=[C:20]([C:22]2[CH:23]=[CH:24][C:25]([C:28]([NH:30][CH2:31][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])=[O:29])=[N:26][CH:27]=2)[CH:21]=1.[Br:40][C:41]1[CH:47]=[CH:46][C:44]([NH2:45])=[C:43]([F:48])[CH:42]=1.CC(O)=O>CCOC(C)=O.ClCCCl>[Br:40][C:41]1[CH:47]=[CH:46][C:44]([NH:45][CH2:38][C:19]2[CH:18]=[CH:17][C:16]([Cl:15])=[CH:21][C:20]=2[C:22]2[CH:23]=[CH:24][C:25]([C:28]([NH:30][CH2:31][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])=[O:29])=[N:26][CH:27]=2)=[C:43]([F:48])[CH:42]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 1230504-Bromo-2-fluoroanilineHCID 5049666Sodium triacetoxyborohydrideHCID 86674246Ethyl 3-(5-(5-chloro-2-formylphenyl)picolinamido)propanoate

Product 1

HCID 71059944Ethyl 3-(5-(2-(((4-bromo-2-fluorophenyl)amino)methyl)-5-chlorophenyl)picolinamido)propanoate

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Solid NaBH(OAc)3 (623 mg, 2.9 mmol) was added to a DCE solution (3 mL) of ethyl 3-(5-(5-chloro-2-formylphenyl)picolinamido)propanoate, prepared as describe in Example 6, (530 mg, 1.5 mmol), 4-bromo-2-fluoroaniline (293 g, 1.5 mmol), and AcOH (0.34 mL, 5.9 mmol) and the resulting mixture was stirred at room temperature. After 16 h the resulting mixture diluted with EtOAc washed with water and brine, dried (Na2SO4), dry-packed onto silica gel and purified via column chromatography to yield the title compound.

Workup

  1. customprepared
  2. washwashed with water and brine
  3. dry with materialdried (Na2SO4)
  4. customdry-packed onto silica gel and purified via column chromatography

Sources & evidence

ORD record
ord-8c2df863289d440eaae1917cecead34c
Source dataset
uspto-grants-2014_06
Patent number
US08748624B2

Reaction notes

Loading…