Acetic Acid → HCID 178505872, compound

HRID 2043358Notes

Reaction equation

HRID 2043358 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[CH:9]([C:11]1[N:12]=[CH:13][NH:14][CH:15]=1)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClCCCl>[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][CH2:9][C:11]2[N:12]=[CH:13][NH:14][CH:15]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 97314-FluoroanilineHCID 764281H-Imidazole-4-carbaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 178505872HCID 178505872, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 4-fluoroaniline (0.60 g, 5.40 mmol) in 1,2-dichloroethane (5 ml) were added 4-formylimidazole (0.78 g, 8.10 mmol), sodium triacetoxyborohydride (2.29 g, 10.8 mmol) and acetic acid (0.06 ml). The reaction mixture was stirred at 50° C. for 4 h. The reaction mixture was then concentrated in vacuo and the residue was purified using flash chromatography (column: Isolute® Flash-NH2 (Separtis); eluent: methanol/dichloromethane gradient) to yield a white solid (160 mg, 16%); MS (ISP): 192.2 ((M+H)+.).

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. customthe residue was purified

Sources & evidence

ORD record
ord-2b7eda71107247ec861a26ebd015ea3d
Source dataset
uspto-grants-2013_11
Patent number
US08586617B2

Reaction notes

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