Potassium Carbonate → HCID 46311864, compound

HRID 1630746Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[CH:6][CH:7]=1.COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1.C(=O)([O-])[O-].[K+].[K+].Cl[C:47]1[C:52]([NH2:53])=[CH:51][CH:50]=[C:49]([CH3:54])[N:48]=1>CC([O-])=O.CC([O-])=O.[Pd+2].O.C(#N)C>[F:1][C:2]1[CH:3]=[C:4]([C:47]2[C:52]([NH2:53])=[CH:51][CH:50]=[C:49]([CH3:54])[N:48]=2)[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 78 °C

Procedure

To a mixture of 3-fluorophenylboronic acid (1.6 g, 12 mmol), S—PHOS (0.304 g, 0.74 mmol), potassium carbonate (3.41 g, 25 mmol), 2-chloro-6-methylpyridin-3-amine 16 (1.3 g, 9.1 mmol), and Pd(OAc)2 (0.085 g, 0.38 mmol) was added acetonitrile (14 mL) and water (9 mL). The reaction mixture was degassed by bubbling nitrogen through the solution for 10 min and the reaction mixture was heated to 78° C. After 4 h, the reaction mixture was diluted with EtOAc, washed with brine (1×), dried over MgSO4, filtered, and concentrated. Purification by flash column chromatography on silica gel (10% to 50% EtOAc in hexanes) gave 2-(3-fluorophenyl)-6-methylpyridin-3-amine.

Workup

customThe reaction mixture was degassed
customby bubbling nitrogen through the solution for 10 min
additionthe reaction mixture was diluted with EtOAc
washwashed with brine (1×)
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated
customPurification by flash column chromatography on silica gel (10% to 50% EtOAc in hexanes)

Sources & evidence

ORD record: ord-bf74b374d36e48aba7bccd73ffa7a023
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08791147B2

Reaction notes

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