Cesium carbonate → HCID 59321127, compound

HRID 341214Notes

Reaction equation

I[C:2]1[N:6]2[CH:7]=[CH:8][C:9]([C:11]3[N:12]=[N:13][N:14]([CH3:16])[N:15]=3)=[CH:10][C:5]2=[N:4][CH:3]=1.CC1(C)C(C)(C)OB([C:25]2[CH:26]=[C:27]([NH:31][C:32]([NH:34][CH2:35][C:36]([F:39])([F:38])[F:37])=[O:33])[CH:28]=[CH:29][CH:30]=2)O1.C([O-])([O-])=O.[Cs+].[Cs+]>COCCOC>[CH3:16][N:14]1[N:13]=[N:12][C:11]([C:9]2[CH:8]=[CH:7][N:6]3[C:2]([C:29]4[CH:28]=[C:27]([NH:31][C:32]([NH:34][CH2:35][C:36]([F:37])([F:38])[F:39])=[O:33])[CH:26]=[CH:25][CH:30]=4)=[CH:3][N:4]=[C:5]3[CH:10]=2)=[N:15]1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 3-iodo-7-(2-methyl-2H-tetrazol-5-yl)-imidazo[1,2-a]pyridine (170 mg, 0.52 mmol), 1-[3-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-3-(2,2,2-trifluoro-ethyl)-urea (16, 225 mg, 0.65 mmol) and Cs2CO3 (340 mg, 1.04 mmol) in dry DME (2.5 ml) was deoxygenated by evacuate/fill N2 (×2). PdCl2dppf (38 mg, 0.05 mmol) was added, and the mixture was deoxygenated again (×3). The reaction was stirred and heated at 80° C. for 16 hours. After cooling to RT the mixture was partitioned between EtOAc/H2O. The aqueous layer was extracted with EtOAc (×2). The combined EtOAc extracts were dried (Na2SO4) and filtered and evaporated. The residue was purified by preparative HPLC to give the title compound (60 mg) as a solid.

Workup

customwas deoxygenated
customby evacuate/fill N2 (×2)
customthe mixture was deoxygenated again (×3)
temperatureAfter cooling to RT the mixture
customwas partitioned between EtOAc/H2O
extractionThe aqueous layer was extracted with EtOAc (×2)
dry with materialThe combined EtOAc extracts were dried (Na2SO4)
filtrationfiltered
customevaporated
customThe residue was purified by preparative HPLC

Sources & evidence

ORD record: ord-64f4db405ab94c15a2ca074923d605ce
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08895745B2

Reaction notes

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