Cesium carbonate → HCID 89442483, compound

HRID 2283941Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[N:15]([CH2:20][CH2:21][OH:22])[CH:16]=[C:17](Br)[N:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:23][C:24]1[CH:25]=[C:26](B(O)O)[CH:27]=[CH:28][C:29]=1[CH3:30].C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.O.C(P(CCCC)CCCC)CCC.C(P(CCCC)CCCC)CCC.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[N:15]([CH2:20][CH2:21][OH:22])[CH:16]=[C:17]([C:27]3[CH:26]=[CH:25][C:24]([F:23])=[C:29]([CH3:30])[CH:28]=3)[N:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 4-[4-bromo-1-(2-hydroxyethyl)-1H-imidazol-2-yl]-piperidine-1-carboxylic acid tert-butyl ester (1600.00 mg; 4.27 mmol; 1.00 eq.), 3-fluoro-4-methyl phenyl boronic acid (855.55 mg; 5.56 mmol; 1.30 eq.), palladium bis(tributylphosphine) (436.95 mg; 0.85 mmol; 0.20 eq.) and Cesium carbonate (4178.60 mg; 12.82 mmol; 3.00 eq.) in 1,4-Dioxane (10.0 mL) and water (1.50 mL) in the sealed vial was stirred at 70° C. for 5 hours. The crude was purified through flash chromatography (EtOAc in Hexanes 30% to 80%) to provide the title compound (1.2 g, 70%).

Workup

customThe crude was purified through flash chromatography (EtOAc in Hexanes 30% to 80%)

Sources & evidence

ORD record: ord-83f6b557fe0a4a989358928f63abde2a
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09145392B2

Reaction notes

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