Acetic Acid → HCID 71059989, compound

HRID 405152

Reaction equation

HRID 405152 reaction equation
[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[CH:15]([C:17]1[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][C:18]=1[C:27]1[CH:28]=[CH:29][C:30]([C:33]([NH:35][CH2:36][CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39])=[O:34])=[N:31][CH:32]=1)=O.[Cl:43][C:44]1[CH:45]=[C:46]([CH:48]=[CH:49][C:50]=1[I:51])[NH2:47].CC(O)=O>CCOC(C)=O.ClCCCl>[Cl:43][C:44]1[CH:45]=[C:46]([NH:47][CH2:15][C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:25])([F:24])[F:26])=[CH:19][C:18]=2[C:27]2[CH:28]=[CH:29][C:30]([C:33]([NH:35][CH2:36][CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39])=[O:34])=[N:31][CH:32]=2)[CH:48]=[CH:49][C:50]=1[I:51]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 2829263-Chloro-4-iodoanilineHCID 5049666Sodium triacetoxyborohydrideHCID 86674249Ethyl 3-(5-(2-formyl-5-(trifluoromethyl)phenyl)picolinamido)propanoate

Product 1

HCID 71059989HCID 71059989, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Solid NaBH(OAc)3 (4.2 g, 19.8 mmol) was added to a DCE solution (45 mL) of ethyl 3-(5-(2-formyl-5-(trifluoromethyl)phenyl)picolinamido)propanoate, prepared as described in Example 22, (3.9 g, 9.9 mmol), 3-chloro-4-iodoaniline (3.0 g, 11.9 mmol), and AcOH (2.8 mL, 49.4 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), 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-bc7dc30af90344f7ab6ed321af29492a
Source dataset
uspto-grants-2014_06
Patent number
US08748624B2

Linked notes

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