Potassium Carbonate → HCID 58924949, compound

HRID 1990999Notes

Reaction equation

HRID 1990999 reaction equation
I[C:2]1[S:3][CH:4]=[C:5]([C:7]([N:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]2[CH3:15])=[O:8])[N:6]=1.[CH3:16][O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1B(O)O.C(=O)([O-])[O-].[K+].[K+]>C(COC)OC>[CH3:16][O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[C:2]1[S:3][CH:4]=[C:5]([C:7]([N:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]2[CH3:15])=[O:8])[N:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27339582-Methoxyphenylboronic acidHCID 58924819HCID 58924819, compound

Product 1

HCID 58924949HCID 58924949, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
78 °C

Procedure

A mixture of (2-iodo-thiazol-4-yl)-(2-methyl-piperidin-1-yl)-methanone (Step 3; 200 mg, 0.59 mmol), 2-methoxyphenylboronic acid (Combi-Blocks, Inc., San Diego, Calif.; 135 mg, 0.89 mmol), potassium carbonate (201 mg, 1.45 mmol), and PdCl2dppf (Strem Chemicals, Inc., Newburyport, Mass.; 22 mg, 0.03 mmol) in dimethoxyethane (3 mL) in a scintillation vial was heated at ˜78° C. for 72 h with shaking. The reaction mixture was cooled to room temperature, concentrated in vacuo using a Genevac evaporator, and purified using automated mass-directed LC-MS purification.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated in vacuo
  3. customa Genevac evaporator
  4. custompurified
  5. custommass-directed LC-MS purification

Sources & evidence

ORD record
ord-b1afd8ff2750474290521a2194e89f9a
Source dataset
uspto-grants-2010_01
Patent number
US07645773B2

Reaction notes

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