Potassium Carbonate → HCID 54590828, compound

HRID 2276750Notes

Reaction equation

HRID 2276750 reaction equation
Br[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:12][CH2:11][CH2:10]2)[CH:3]=1.[C:19]1(B(O)O)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+].O1CCOCC1>C(=O)(O)[O-].[Na+].O>[C:19]1([C:2]2[CH:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]3([C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=4)[CH2:12][CH2:11][CH2:10]3)[CH:3]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 66827Phenylboronic AcidHCID 67454264HCID 67454264, compound

Product 1

HCID 54590828HCID 54590828, compoundYield 18.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
140 °C

Procedure

To a 3 mL microwave reaction vessel was added 4-bromo-N-(1-phenylcyclobutyl)pyridin-2-amine (50 mg, 165 μmol, 1.0 equiv), phenylboronic acid (30 mg, 248 μmol, 1.5 equiv), Cl2Pd(dppf) (12 mg, 16 μmol, 0.1 equiv), potassium carbonate (57 mg, 413 μmol, 2.5 equiv), dioxane (750 μL), and water (250 μL). The reaction was heated in a microwave reactor at 140° C. for 20 min and then diluted with saturated sodium bicarbonate (20 mL) and extracted with ethyl acetate (50 mL). The organic layer was then dried over Na2SO4, filtered, and concentrated to give a crude solid that was purified by reverse phase column chromatography to afford 9 mg of 4-phenyl-N-(1-phenylcyclobutyl)pyridin-2-amine (m/z [M+H]=301.2).

Workup

  1. extractionextracted with ethyl acetate (50 mL)
  2. dry with materialThe organic layer was then dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give a crude solid that
  6. customwas purified by reverse phase column chromatography

Sources & evidence

ORD record
ord-56ac509b47844cf3ae6950026c8d58f9
Source dataset
uspto-grants-2015_09
Patent number
US09133123B2

Reaction notes

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