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

HRID 405177Notes

Reaction equation

HRID 405177 reaction equation
[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[CH:15]([C:17]1[CH:22]=[C:21]([O:23][CH3:24])[CH:20]=[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]=[C:21]([O:23][CH3:24])[CH:20]=[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 86674255Ethyl 3-(5-(2-formyl-4-methoxyphenyl)picolinamido)propanoate

Product 1

HCID 71059897Ethyl 3-(5-(2-(((4-bromophenyl)amino)methyl)-4-methoxyphenyl)picolinamido)propanoate

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Solid NaBH(OAc)3 (446 mg, 2.1 mmol) was added to a DCE solution (7 mL) of ethyl 3-(5-(2-formyl-4-methoxyphenyl)picolinamido)propanoate, prepared as in Example 58 (500 mg, 1.4 mmol), 4-bromoaniline (362 mg, 2.1 mmol), and AcOH (0.08 mL, 1.4 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-773cd95869894ebf8d361451da961fd3
Source dataset
uspto-grants-2014_06
Patent number
US08748624B2

Reaction notes

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