Potassium Carbonate → HCID 67233759, compound

HRID 2368750Notes

Reaction equation

HRID 2368750 reaction equation
[CH2:1]([O:5][C:6]([C:8]1[C:9]([OH:18])=[C:10]2[CH:17]=[CH:16][S:15][C:11]2=[C:12](Br)[N:13]=1)=[O:7])[CH2:2][CH2:3][CH3:4].[CH3:19]B1OB(C)OB(C)O1.C(=O)([O-])[O-].[K+].[K+]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O1CCOCC1>[CH2:1]([O:5][C:6]([C:8]1[C:9]([OH:18])=[C:10]2[CH:17]=[CH:16][S:15][C:11]2=[C:12]([CH3:19])[N:13]=1)=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 574072TrimethylboroxineHCID 86607517HCID 86607517, compound

Product 1

HCID 67233759HCID 67233759, compound

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 7-bromo-4-hydroxy-thieno[2,3-c]pyridine-5-carboxylic acid butyl ester (example 43 a, 165 mg, 0.5 mmol), trimethylboroxine (70 μl, 0.5 mmol), tetrakis(triphenylphosphine) palladium(0) (118 mg, 0.1 mmol), potassium carbonate (208 mg, 1.5 mmol), and anhydrous 1.4-dioxane (3 ml) was heated in a microwave oven at 140° C. for 15 min. Then silica gel was added and the mixture concentrated in vacuo. The residue was added on top of a short column filled with silica gel. Elution with ethyl acetate:hexanes=9:1 and in vacuo concentration gave the title compound as a yellowish oil; MS-(+)-ion: MS-(+)-ion: M+1=266.0.

Workup

  1. additionThen silica gel was added
  2. concentrationthe mixture concentrated in vacuo
  3. additionThe residue was added on top of a short column
  4. additionfilled with silica gel
  5. washElution with ethyl acetate
  6. concentrationhexanes=9:1 and in vacuo concentration

Sources & evidence

ORD record
ord-8caacc507da644cf9b31e7e6e3b87a7b
Source dataset
uspto-grants-2014_04
Patent number
US08703795B2

Reaction notes

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