Potassium Carbonate → N-(2-(4-fluorophenyl)-2-methylpropyl)-5-vinylpyridin-2-amine

HRID 2276753Notes

Reaction equation

Br[C:2]1[CH:3]=[N:4][C:5]([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])=N[CH:7]=1.[CH:20](B1OB(C=C)OB(C=C)O1)=[CH2:21].[C:32](=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[F:19][C:16]1[CH:15]=[CH:14][C:13]([C:10]([CH3:11])([CH3:12])[CH2:9][NH:8][C:5]2[CH:21]=[CH:20][C:2]([CH:7]=[CH2:32])=[CH:3][N:4]=2)=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 115 °C

Procedure

To a 5 mL microwave reaction vessel was added 5-bromo-N-(2-(4-fluorophenyl)-2-methylpropyl)pyrimidin-2-amine (255 mg, 0.8 mmol, 1.0 equiv), 2,4,6-trivinyl-1,3,5,2,4,6-trioxatriborinane (285 mg, 1.2 mmol, 1.5 equiv), Cl2Pd(dppf) (58 mg, 79 μmol, 0.1 equiv), potassium carbonate (1.2 mL of a 2N aqueous solution, 2.4 mmol, 3.0 equiv), and dioxane (4 mL). The reaction was heated in a microwave reactor at 115° C. for 20 min. The aqueous layer was removed from the reaction, and the organic layer was directly purified by reverse phase column chromatography to give 158 mg (73%) of N-(2-(4-fluorophenyl)-2-methylpropyl)-5-vinylpyridin-2-amine.

Workup

customThe aqueous layer was removed from the reaction
customthe organic layer was directly purified by reverse phase column chromatography

Sources & evidence

ORD record: ord-461da193970b4a85a5f5b457564b2658
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133123B2

Reaction notes

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