Potassium Phosphate, Tribasic → 1-(3-(7-Chloroimidazo[1,2-a]pyridin-3-yl)phenyl)-3-(2,2,2-trifluoroethyl)urea

HRID 2400321Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][N:5]2[C:8](I)=[CH:9][N:10]=[C:4]2[CH:3]=1.CC1(C)C(C)(C)OB([C:20]2[CH:21]=[C:22]([NH:26][C:27]([NH:29][CH2:30][C:31]([F:34])([F:33])[F:32])=[O:28])[CH:23]=[CH:24][CH:25]=2)O1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.O.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:24]3[CH:23]=[C:22]([NH:26][C:27]([NH:29][CH2:30][C:31]([F:32])([F:33])[F:34])=[O:28])[CH:21]=[CH:20][CH:25]=3)=[CH:9][N:10]=[C:4]2[CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 7-Chloro-3-iodo-imidazo[1,2-a]pyridine (15.17 g, 54.5 mmol) in 1,4-dioxane (260 ml) was added 1-[3-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-3-(2,2,2-trifluoro-ethyl)-urea (22.5 g, 65.4 mmol) and aqueous K3PO4 (23.1 g in 65 ml H2O, 109 mmol) [reaction degassed by bubbling N2 through] followed by 1,1′-bis(diphenylphosphino)ferrocene palladium (II) chloride (1.99 g, 2.72 mmol). The mixture was heated at 80° C. overnight, then diluted with water and extracted with EtOAc. The organic layer was washed with brine, dried (MgSO4), filtered and concentrated under reduced pressure. The residue was triturated with DCM (100 ml), filtered and the filtercake washed with 1:1 DCM:Petroleum ether to give the product (13.2 g) as a beige solid. MS: [M+H]+=369.

Workup

extractionextracted with EtOAc
washThe organic layer was washed with brine
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue was triturated with DCM (100 ml)
filtrationfiltered
washthe filtercake washed with 1:1 DCM

Sources & evidence

ORD record: ord-ba083af4a5a64a0490842d28496eebd8
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08796244B2

Reaction notes

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