Cesium carbonate → N-(4-(3-(2-methylpyridin-4-yl)pyrazin-2-yloxy)phenyl)pyridin-2-amine

HRID 473633Notes

Reaction equation

HRID 473633 reaction equation
Cl[C:2]1[C:3]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=3)=[CH:11][CH:10]=2)=[N:4][CH:5]=[CH:6][N:7]=1.[CH3:22][C:23]1[CH:28]=[C:27](B(O)O)[CH:26]=[CH:25][N:24]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>COCCOC.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:22][C:23]1[CH:28]=[C:27]([C:2]2[C:3]([O:8][C:9]3[CH:14]=[CH:13][C:12]([NH:15][C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=4)=[CH:11][CH:10]=3)=[N:4][CH:5]=[CH:6][N:7]=2)[CH:26]=[CH:25][N:24]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 41926642-Methylpyridine-4-boronic acidHCID 53485989N-(4-(3-chloropyrazin-2-yloxy)phenyl)pyridin-2-amine

Product 1

HCID 59374298N-(4-(3-(2-methylpyridin-4-yl)pyrazin-2-yloxy)phenyl)pyridin-2-amine

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a 50 mL round-bottomed flask was added N-(4-(3-chloropyrazin-2-yloxy)phenyl)pyridin-2-amine (0.2890 g, 0.967 mmol), 2-methylpyridin-4-ylboronic acid (0.1684 g, 1.20 mmol), and trans-dichlorobis(triphenylphosphine)palladium (II) (0.0355 g, 0.0484 mmol) in DME. An aqueous solution of cesium carbonate (0.213 ml, 2.61 mmol) was added and the temperature was brought to 80° C. to stir overnight. The crude product was adsorbed onto a plug of silica gel and chromatographed to provide N-(4-(3-(2-methylpyridin-4-yl)pyrazin-2-yloxy)phenyl)pyridin-2-amine. MS (ESI, pos. ion) m/z: 356.1. IC50 (uM)=0.033.

Workup

  1. customwas brought to 80° C.
  2. customchromatographed

Sources & evidence

ORD record
ord-104e7c8489ed499ca6fe9fac1a65690d
Source dataset
uspto-grants-2014_01
Patent number
US08637500B2

Reaction notes

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