Diisopropylethylamine → HCID 117839986, compound

HRID 1477659Notes

Reaction equation

HRID 1477659 reaction equation
[N+:1]([C:4]1[CH:8]=[CH:7][NH:6][CH:5]=1)([O-:3])=[O:2].[F:9][C:10]1[CH:15]=[CH:14][C:13](B(O)O)=[CH:12][CH:11]=1.C(N(CC)C(C)C)(C)C>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.ClCCl>[F:9][C:10]1[CH:15]=[CH:14][C:13]([N:6]2[CH:7]=[CH:8][C:4]([N+:1]([O-:3])=[O:2])=[CH:5]2)=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 1458133-NitropyrroleHCID 2856454-Fluorophenylboronic acid

Product 1

HCID 117839986HCID 117839986, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a dichloromethane solution (4.0 mL) of 3-nitropyrrole (200 mg, 1.78 mmol), 4-fluorophenylboronic acid (499 mg, 3.57 mmol), and copper acetate (II) (486 mg, 2.68 mmol), N,N-diisopropylethylamine (606 μL, 3.57 mmol) was added and the resultant mixture was stirred at room temperature for 1 day. After completion of the reaction, the reaction solution was filtered with Celite and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1) to obtain the title compound (131 mg, yield 36%).

Workup

  1. customAfter completion of the reaction
  2. filtrationthe reaction solution was filtered with Celite
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-7f5e5adf61d047e2be66ea13bff8b2fd
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

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