Acetic Acid → HCID 10281896, compound

HRID 1839476Notes

Reaction equation

HRID 1839476 reaction equation
[F:1][C:2]([F:19])([F:18])[O:3][C:4]1[CH:5]=[C:6]([CH:15]=[CH:16][CH:17]=1)[O:7][C:8]1[CH:9]=[C:10]([CH:12]=[CH:13][CH:14]=1)[NH2:11].[F:20][C:21]([F:34])([O:25][C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][CH:33]=1)[CH:29]=O)[CH:22]([F:24])[F:23].C(O[BH-](O[C:45](=[O:47])[CH3:46])OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClC(Cl)C>[F:1][C:2]([F:18])([F:19])[O:3][C:4]1[CH:5]=[C:6]([CH:15]=[CH:16][CH:17]=1)[O:7][C:8]1[CH:9]=[C:10]([N:11]([CH2:29][C:28]2[CH:31]=[CH:32][CH:33]=[C:26]([O:25][C:21]([F:34])([F:20])[CH:22]([F:24])[F:23])[CH:27]=2)[CH2:46][C@@H:45]([OH:47])[C:2]([F:19])([F:18])[F:1])[CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 118803Benzaldehyde, 3-(1,1,2,2-tetrafluoroethoxy)-HCID 5049666Sodium triacetoxyborohydrideHCID 108801183-(3-trifluoromethoxyphenoxy)aniline

Product 1

HCID 10281896HCID 10281896, compoundYield 165.6%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

EX-19C) To a solution of 3-(3-trifluoromethoxyphenoxy)aniline (1.0 g, 3.7 mmol) from EX-19B and 3-(1,1,2,2-tetrafluoroethoxy)benzaldehyde (0.83 g, 3.7 mmol) in 18.5 mL of dichloroethane was added sodium triacetoxyborohydride (1.0 g, 4.7 mmol) and glacial acetic acid (0.25 mL, 4.3 mmol). The reaction mixture was stirred at room temperature overnight then quenched with saturated aqueous sodium bicarbonate and extracted with methylene chloride. The organic layer was dried over MgSO4 and concentrated in vacuo to give 1.8 g (100%) of the desired [3-(3-trifluoromethoxy-phenoxy)phenyl][[3-(1,1,2,2-tetrafluoroethoxy)phenyl]methyl]amine product as a yellow oil, which was greater than 90% pure by reverse phase HPLC analysis. HRMS calcd. for C22H16F7NO3: 476.1097 [M+H]+, found: 476.1069. This material was carried on to the next step without further purification.

Workup

  1. customthen quenched with saturated aqueous sodium bicarbonate
  2. extractionextracted with methylene chloride
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bc2df1bd032e4aaba11f02ed35fddf57
Source dataset
uspto-grants-2004_01
Patent number
US06677341B2

Reaction notes

Loading…