Dinitrofluorobenzene → HCID 58653674, compound

HRID 1676083Notes

Reaction equation

HRID 1676083 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1F)([O-:3])=[O:2].C(N(CC)C(C)C)(C)C.[NH2:23][CH:24]([C:30]1[CH:35]=[CH:34][C:33]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[CH:32][CH:31]=1)[CH2:25][C:26]([O:28][CH3:29])=[O:27]>CO>[C:33]1([C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH:34]=[CH:35][C:30]([CH:24]([NH:23][C:5]2[CH:6]=[CH:7][C:8]([N+:10]([O-:12])=[O:11])=[CH:9][C:4]=2[N+:1]([O-:3])=[O:2])[CH2:25][C:26]([O:28][CH3:29])=[O:27])=[CH:31][CH:32]=1

Participants

5

Reactant 3

HCID 6264DinitrofluorobenzeneHCID 81531DiisopropylethylamineHCID 10999647HCID 10999647, compound

Product 1

HCID 58653674HCID 58653674, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2,4-dinitrofluorobenzene (247 mg, 847 μmol) in methanol (2 mL) was added N,N-diisopropylethylamine (147 μL, 844 μmol) and methyl 3-amino-3-(1,1′-biphenyl)-4-ylpropanoate (158 mg, 849 μmol). The solution was stirred at room temperature for 72 hours, then evaporated in vacuo. The residue was purified by flash column chromatography on silica gel, eluting with a mixture of petroleum ether and dichloromethane (1:1 to 0:1), to afford the title compound, [LCMS (Method B, Mobile Phase I) RT=3.81 min, MH+ 422].

Workup

  1. customevaporated in vacuo
  2. customThe residue was purified by flash column chromatography on silica gel
  3. washeluting with a mixture of petroleum ether and dichloromethane (1:1 to 0:1)

Sources & evidence

ORD record
ord-38b62b220c5547c1b5c440021f166d99
Source dataset
uspto-grants-2011_08
Patent number
US08003806B2

Reaction notes

Loading…