Thiophene-3-boronic acid → Methyl 5-(thiophen-3-yl)pyridine-3-carboxylate

HRID 1976594Notes

Reaction equation

HRID 1976594 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C:4]1(Br)[CH:9]=[CH:8][CH:7]=[N:6][CH2:5]1.[S:12]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13]1>O1CCOCC1>[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[C:8]([C:14]2[CH:15]=[CH:16][S:12][CH:13]=2)[CH:7]=[N:6][CH:5]=1

Participants

4

Reactant 2

HCID 581760Thiophene-3-boronic acidHCID 23436229HCID 23436229, compound

Product 1

HCID 23004855Methyl 5-(thiophen-3-yl)pyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

Methyl-3-bromo-nicotinate and 3-thiophene boronic acid were dissolved in degassed dioxane (25 mL). To the homogeneous solution was added Pd((Ph3)4P)). The reaction was heated to 90° C. for 18 hours and then cooled to room temperature and concentrated. The residue was taken up into EtOAc and water. The layers were then separated and the organics washed with brine and dried (MgSO4). Flash LC (60% Hexanes/EtOAc) gave the desired product.

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated
  3. customThe layers were then separated
  4. washthe organics washed with brine
  5. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-5f86f036c18f4dd29a7537145d3857c0
Source dataset
uspto-grants-2001_05
Patent number
US06228871B1

Reaction notes

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