1-Methyl-5-(tri-n-butylstannyl)imidazole → N-(4-(3-(1-Methyl-1H-imidazol-5-YL)pyrazin-2-yloxy)phenyl)pyridin-2-amine

HRID 473637Notes

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][N:23]1[C:27]([Sn](CCCC)(CCCC)CCCC)=[CH:26][N:25]=[CH:24]1>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:22][N:23]1[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][N:25]=[CH:24]1

Participants

Conditions

Temperature: 160 °C

Procedure

A suspension of N-(4-(3-chloropyrazin-2-yloxy)phenyl)pyridin-2-amine (350 mg, 1172 μmol), 1-methyl-5-(tributylstannyl)-1H-imidazole (870 mg, 2343 μmol), and tetrakis(triphenylphosphine)palladium (0) (271 mg, 234 μmol) in 1,4-dioxane (4 mL) was sparged with argon for 3 minutes then the vessel was appropriately sealed. The vessel was then heated to 160° C. with microwaves (3 bar; 130 watts) for 20 minutes. The solvents were removed under reduced pressure and the residue was purified on silica (40 g) eluting products with 2-4% of MeOH/DCM to afford the title compound as a white solid. MS (ESI pos. ion) m/z: 345.1 (M+1). IC50 (uM) 0.034.

Workup

customwas sparged with argon for 3 minutes
customthe vessel was appropriately sealed
customThe solvents were removed under reduced pressure
customthe residue was purified on silica (40 g)
washeluting products with 2-4% of MeOH/DCM

Sources & evidence

ORD record: ord-85897abb7d9a466cadb2aaa97ced07c2
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637500B2

Reaction notes

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