Potassium Carbonate → HCID 54591864, compound

HRID 2276748Notes

Reaction equation

Br[C:2]1[N:7]=[C:6]([NH:8][CH2:9][C:10]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)([CH3:12])[CH3:11])[CH:5]=[CH:4][CH:3]=1.[CH3:20][C:21]([CH3:26])=[CH:22]B(O)O.C(=O)([O-])[O-].[K+].[K+].O1CCOCC1>C(=O)(O)[O-].[Na+].O>[F:19][C:16]1[CH:17]=[CH:18][C:13]([C:10]([CH3:12])([CH3:11])[CH2:9][NH:8][C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([CH:20]=[C:21]([CH3:26])[CH3:22])[N:7]=2)=[CH:14][CH:15]=1

Participants

Conditions

Temperature: 135 °C

Procedure

To a 5 mL microwave reaction vessel was added 6-bromo-N-(2-(4-fluorophenyl)-2-methylpropyl)pyridin-2-amine (220 mg, 0.7 mmol, 1.0 equiv), 2-methylprop-1-enylboronic acid (100 mg, 1 mmol, 1.5 equiv), Cl2Pd(dppf) (50 mg, 70 μmol, 0.1 equiv), potassium carbonate (300 mg, 2.1 mmol, 3.0 equiv), dioxane (4 mL), and water (1 mL). The reaction was heated in a microwave reactor at 135° C. for 35 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 14 mg of N-(2-(4-fluorophenyl)-2-methylpropyl)-6-(2-methylprop-1-enyl)pyridin-2-amine (m/z [M+H]=299.4).

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 reverse phase column chromatography

Sources & evidence

ORD record: ord-2c55e40b850c4c419e1bcea5e4a33352
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133123B2

Reaction notes

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