Acetic Acid → Ethyl 3-(5-(2-(((4-bromophenyl)amino)methyl)-5-methoxyphenyl)picolinamido)propanoate

HRID 405165Notes

Reaction equation

HRID 405165 reaction equation
[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[CH:15]([C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][C:18]=1[C:25]1[CH:26]=[CH:27][C:28]([C:31]([NH:33][CH2:34][CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])=[O:32])=[N:29][CH:30]=1)=O.[Br:41][C:42]1[CH:48]=[CH:47][C:45]([NH2:46])=[CH:44][CH:43]=1.CC(O)=O>CCOC(C)=O.ClCCCl>[Br:41][C:42]1[CH:48]=[CH:47][C:45]([NH:46][CH2:15][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][C:18]=2[C:25]2[CH:26]=[CH:27][C:28]([C:31]([NH:33][CH2:34][CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])=[O:32])=[N:29][CH:30]=2)=[CH:44][CH:43]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 78074-BromoanilineHCID 5049666Sodium triacetoxyborohydrideHCID 86674253Ethyl 3-(5-(2-formyl-5-methoxyphenyl)picolinamido)propanoate

Product 1

HCID 71060028Ethyl 3-(5-(2-(((4-bromophenyl)amino)methyl)-5-methoxyphenyl)picolinamido)propanoate

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Solid NaBH(OAc)3 (1.3 g, 6.0 mmol) was added to a DCE solution (5 mL) of ethyl 3-(5-(2-formyl-5-methoxyphenyl)picolinamido)propanoate (1.4 g, 4.0 mmol), 4-bromoaniline (1.0 g, 6.0 mmol), and AcOH (0.23 mL, 4.0 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), concentrated and purified via column chromatography to yield the title compound.

Workup

  1. washwashed with water and brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. custompurified via column chromatography

Sources & evidence

ORD record
ord-5ba8018c02214ce9844a20e02cc53329
Source dataset
uspto-grants-2014_06
Patent number
US08748624B2

Reaction notes

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