Acetic Acid → Methyl 5-(2-(((4-bromo-3-fluorophenyl)amino)methyl)-5-fluorophenyl)picolinate

HRID 405169Notes

Reaction equation

HRID 405169 reaction equation
[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[F:15][C:16]1[CH:17]=[CH:18][C:19]([CH:32]=O)=[C:20]([C:22]2[CH:23]=[CH:24][C:25]([C:28]([O:30][CH3:31])=[O:29])=[N:26][CH:27]=2)[CH:21]=1.[Br:34][C:35]1[CH:41]=[CH:40][C:38]([NH2:39])=[CH:37][C:36]=1[F:42].CC(O)=O>CCOC(C)=O.ClCCCl>[Br:34][C:35]1[CH:41]=[CH:40][C:38]([NH:39][CH2:32][C:19]2[CH:18]=[CH:17][C:16]([F:15])=[CH:21][C:20]=2[C:22]2[CH:23]=[CH:24][C:25]([C:28]([O:30][CH3:31])=[O:29])=[N:26][CH:27]=2)=[CH:37][C:36]=1[F:42]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8218484-Bromo-3-fluoroanilineHCID 5049666Sodium triacetoxyborohydrideHCID 86674254HCID 86674254, compound

Product 1

HCID 71060114Methyl 5-(2-(((4-bromo-3-fluorophenyl)amino)methyl)-5-fluorophenyl)picolinate

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Solid NaBH(OAc)3 (491 mg, 2.3 mmol) was added to a DCE solution (4 mL) of methyl 5-(5-fluoro-2-formylphenyl)picolinate (300 mg, 1.2 mmol), 4-bromo-3-fluoroaniline (242 mg, 1.3 mmol), and AcOH (0.27 mL, 4.6 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-8962f3de38a84cb48e0ff9f948ad15f3
Source dataset
uspto-grants-2014_06
Patent number
US08748624B2

Reaction notes

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