Acetic Acid → {2-[(2,4-Dimethoxybenzyl)amino]-5-methoxyphenyl}(3-fluorophenyl)methanone

HRID 1169685Notes

Reaction equation

HRID 1169685 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=1)=[O:11].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C.[CH3:37][O:38][C:39]1[CH:46]=[C:45]([O:47][CH3:48])[CH:44]=[CH:43][C:40]=1[CH:41]=O>ClC(Cl)C>[CH3:37][O:38][C:39]1[CH:46]=[C:45]([O:47][CH3:48])[CH:44]=[CH:43][C:40]=1[CH2:41][NH:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=1)=[O:11]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 691752,4-DimethoxybenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 39101631(2-Amino-5-methoxyphenyl)(3-fluorophenyl)methanone

Product 1

HCID 68659721{2-[(2,4-Dimethoxybenzyl)amino]-5-methoxyphenyl}(3-fluorophenyl)methanone

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of (2-Amino-5-methoxyphenyl)(3-fluorophenyl)methanone (0.984 g, 4.01 mmol) in 15 mL of dichloroethane was added 4 Å powdered molecular sieves (1 g), followed by sodium triacetoxyborohydride (2.55 g, 12.0 mmol) and acetic acid (0.69 mL, 12.0 mmol). 2,4-Dimethoxybenzaldehyde was added (0.667 g, 4.01 mmol), and the reaction was stirred at room temperature for 3 hours. The reaction was partitioned between EtOAc and saturated NaHCO3 solution, and the organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The titled product was isolated as a red oil (1.66 g) which was used in the next step without further purification. ESI+MS: 396.2 [M+H]+.

Workup

  1. customThe reaction was partitioned between EtOAc and saturated NaHCO3 solution
  2. washthe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a949e62354754daebb34f6813daf425d
Source dataset
uspto-grants-2010_11
Patent number
US07825131B2

Reaction notes

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