2-Bromopyridine → N-(4-(3-(2-Methoxypyridin-3-YL)pyrazin-2-yloxy)phenyl)pyridin-2-amine

HRID 473636Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:8]([C:9]2[C:10]([O:15][C:16]3[CH:22]=[CH:21][C:19]([NH2:20])=[CH:18][CH:17]=3)=[N:11][CH:12]=[CH:13][N:14]=2)=[CH:7][CH:6]=[CH:5][N:4]=1.Br[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=1.CC(C)([O-])C.[Na+]>CC(C1C=C(C(C)C)C(C2C(P(C3CCCCC3)C3CCCCC3)=C(OC)C=CC=2OC)=C(C(C)C)C=1)C.C1C=[C-]C(CCN)=CC=1.Cl[Pd+]>[CH3:1][O:2][C:3]1[C:8]([C:9]2[C:10]([O:15][C:16]3[CH:22]=[CH:21][C:19]([NH:20][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=4)=[CH:18][CH:17]=3)=[N:11][CH:12]=[CH:13][N:14]=2)=[CH:7][CH:6]=[CH:5][N:4]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A glass microwave reaction vessel was charged with 4-(3-(2-methoxypyridin-3-yl)pyrazin-2-yloxy)aniline (0.1874 g, 0.637 mmol), 2-bromopyridine (0.075 mL, 0.764 mmol), BrettPHOS precatalyst (10.19 mg, 0.013 mmol), and sodium tert-butoxide (0.153 g, 1.592 mmol). The flask was placed under vacuum then flushed with argon. Dioxane (2.122 mL) was added and the reaction was heated to 90° C. to stir overnight. The crude product was adsorbed onto a plug of silica gel and chromatographed to give the title compound. MS (ESI, pos. ion) m/z: 372.0, IC50 (uM)=0.002903.

Workup

customA glass microwave reaction vessel
customthen flushed with argon
additionDioxane (2.122 mL) was added
customchromatographed

Sources & evidence

ORD record: ord-f49dc635ea6642ecb5b5c04a2379c2b3
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637500B2

Reaction notes

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