Acetic Acid → HCID 178505873, compound

HRID 2043341Notes

Reaction equation

HRID 2043341 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[F:9])[NH2:5].[CH:10]([C:12]1[N:13]=[CH:14][NH:15][CH:16]=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:3]=[C:4]([NH:5][CH2:10][C:12]2[N:13]=[CH:14][NH:15][CH:16]=2)[CH:6]=[CH:7][C:8]=1[F:9]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 764281H-Imidazole-4-carbaldehydeHCID 774693,4-DifluoroanilineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 178505873HCID 178505873, compoundYield 29.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 3,4-difluoroaniline (0.60 g, 4.65 mmol) in 1,2-dichloroethane (5 ml) were added 4-formylimidazole (0.67 g, 6.97 mmol), sodium triacetoxyborohydride (1.97 g, 9.29 mmol) and acetic acid (0.05 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 an off-white solid (284 mg, 29%); MS (ISP): 210.1 ((M+H)+.).

Workup

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

Sources & evidence

ORD record
ord-638fd86223454ef8a7f76200a98f3a9e
Source dataset
uspto-grants-2013_11
Patent number
US08586617B2

Reaction notes

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