Potassium Carbonate → HCID 54590830, compound

HRID 2276752Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]([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)=[N:6][CH:7]=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:3]=[CH:4][C:5]([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)=[N:6][CH:7]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

Conditions

Temperature: 140 °C

Procedure

To a 3 mL microwave reaction vessel was added 5-bromo-N-(1-phenylcyclobutyl)pyridin-2-amine (102 mg, 340 μmol, 1.0 equiv), phenylboronic acid (59 mg, 505 μmol, 1.5 equiv), Cl2Pd(dppf) (25 mg, 34 μmol, 0.1 equiv), potassium carbonate (116 mg, 842 μmol, 2.5 equiv), dioxane (1 mL) and water (500 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 silica gel column chromatography (10% EtOAc/hexanes), affording 27 mg of 5-phenyl-N-(1-phenylcyclobutyl)pyridin-2-amine as a white solid (m/z [M+H]=301.2).

Workup

extractionextracted with ethyl acetate (50 mL)
dry with materialThe organic layer was then dried over Na2SO4
filtrationfiltered
concentrationconcentrated
customto give a crude solid that
customwas purified by silica gel column chromatography (10% EtOAc/hexanes)

Sources & evidence

ORD record: ord-9cbc4489826c4bf78a0ff5e1e0a8b702
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133123B2

Reaction notes

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