Potassium Carbonate → HCID 67233759, compound

HRID 1465965Notes

Reaction equation

HRID 1465965 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 43a, 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-26374a506ae74906b45fc21def793bc2
Source dataset
uspto-grants-2015_04
Patent number
US09000006B2

Reaction notes

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