Water → HCID 58879966, compound

HRID 1361414Notes

Reaction equation

HRID 1361414 reaction equation
[OH:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[F:11][C:12]1[CH:17]=[CH:16][C:15](B(O)O)=[CH:14][CH:13]=1.N1C=CC=CC=1.O>O1CCOCC1.C([O-])(=O)C.[Cu+]>[F:11][C:12]1[CH:17]=[CH:16][C:15]([N:3]2[CH:4]=[CH:5][CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]2=[O:1])=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 2856454-Fluorophenylboronic acidHCID 178526677HCID 178526677, compound

Product 1

HCID 58879966HCID 58879966, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 69023Cuprous acetateCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-hydroxy-3-nitropyridine (Aldrich, 3.0 mmol, 420 mg) in 1,4-dioxane (20 mL), were added 4-fluorophenyl boronic acid (Combi-block, 6.0 mmol, 840 mg), copper(I) acetate (Aldrich, 4.5 mmol, 815 mg) and pyridine (2 mL). The reaction was heated at 80° C. for 20 h. After cooling to room temperature, 30 mL of cold water was added. The solid formed was collected by filtration, washed with ammonium hydroxide and water, and dried under vacuum to give the desired product (610 mg, 87% yield) as a solid. MS(ESI+) m/z 235.30 (M+H)+.

Workup

  1. temperatureAfter cooling to room temperature
  2. customThe solid formed
  3. filtrationwas collected by filtration
  4. washwashed with ammonium hydroxide and water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-bbd48a10812046fdace98aaca3e8bd58
Source dataset
uspto-grants-2011_02
Patent number
US07880004B2

Reaction notes

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