4-Bromoaniline → Tert-butyl 3-(5-(2-(((4-bromophenyl)amino)methyl)-5-chlorophenyl)picolinamido)propanoate

HRID 405214Notes

Reaction equation

HRID 405214 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:40]=O)=[C:20]([C:22]2[CH:23]=[CH:24][C:25]([C:28]([NH:30][CH2:31][CH2:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])=[O:29])=[N:26][CH:27]=2)[CH:21]=1.[Br:42][C:43]1[CH:49]=[CH:48][C:46]([NH2:47])=[CH:45][CH:44]=1>C(Cl)Cl.C([O-])([O-])=O.[Na+].[Na+]>[Br:42][C:43]1[CH:49]=[CH:48][C:46]([NH:47][CH2:40][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][C:36]([CH3:37])([CH3:38])[CH3:39])=[O:34])=[O:29])=[N:26][CH:27]=2)=[CH:45][CH:44]=1

Participants

6

Reactant 3

HCID 78074-BromoanilineHCID 5049666Sodium triacetoxyborohydrideHCID 86674275Tert-butyl 3-(5-(5-chloro-2-formylphenyl)picolinamido)propanoate

Product 1

HCID 71059988Tert-butyl 3-(5-(2-(((4-bromophenyl)amino)methyl)-5-chlorophenyl)picolinamido)propanoate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 10340Sodium CarbonateSolvent

Procedure

Solid NaBH(OAc)3 (1.4 g, 6.8 mmol) was added to a DCM solution (10 mL) of tert-butyl 3-(5-(5-chloro-2-formylphenyl)picolinamido)propanoate (1.3 g, 3.4 mmol) and 4-bromoaniline (882 mg, 5.1 mmol), and the resulting mixture was stirred at room temperature. After 40 h the resulting mixture diluted with DCM and saturated aqueous Na2CO3 and stirred vigorously. After 5 min, the layers were separated and the aqueous phase was extracted with DCM. The combined organics were washed with water and brine, dried (Na2SO4), concentrated and purified via column chromatography to yield the title compound.

Workup

  1. stirringstirred vigorously
  2. customthe layers were separated
  3. extractionthe aqueous phase was extracted with DCM
  4. washThe combined organics were washed with water and brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. custompurified via column chromatography

Sources & evidence

ORD record
ord-72c64b93d4d345f58a10f68e1171b4ae
Source dataset
uspto-grants-2014_06
Patent number
US08748624B2

Reaction notes

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