Potassium Acetate → HCID 67179790, compound

HRID 2362196Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:29])[CH2:5][CH2:6][C:7]1[N:8]([C:19]2[CH:24]=[CH:23][C:22]([C:25](=[O:27])[NH2:26])=[CH:21][C:20]=2[CH3:28])[C:9]([C:12]2[CH:17]=[CH:16][C:15](I)=[CH:14][CH:13]=2)=[CH:10][CH:11]=1)[CH3:2].[NH:30]1[CH:34]=[CH:33][C:32](B2OC(C)(C)C(C)(C)O2)=[N:31]1.C([O-])(=O)C.[K+]>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[NH:30]1[CH:34]=[C:33]([C:15]2[CH:16]=[CH:17][C:12]([C:9]3[N:8]([C:19]4[CH:24]=[CH:23][C:22]([C:25](=[O:27])[NH2:26])=[CH:21][C:20]=4[CH3:28])[C:7]([CH2:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:29])=[CH:11][CH:10]=3)=[CH:13][CH:14]=2)[CH:32]=[N:31]1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 3-[1-(4-Carbamoyl-2-methyl-phenyl)-5-(4-iodo-phenyl)-1H-pyrrol-2-yl]-propanoic acid ethyl ester (127 mg, 0.252 mmol), 1H-pyrazole boronic acid pinacol ester (147 mg, 0.75 mmol), potassium acetate (222 mg, 2.3 mmol), and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (60.0 mg, 0.074 mmol) in anhydrous DMF (4 mL) was degassed with nitrogen and then heated at 100° C. for 16 h. The mixture was then diluted with ethyl acetate (50 mL) and washed with water (30 mL). After drying the organic layer over anhydrous Na2SO4, the solvent was removed to obtain a crude product which is purified by silica gel flash chromatography (33 mg, 28%).

Workup

customwas degassed with nitrogen
additionThe mixture was then diluted with ethyl acetate (50 mL)
washwashed with water (30 mL)
dry with materialAfter drying the organic layer over anhydrous Na2SO4
customthe solvent was removed

Sources & evidence

ORD record: ord-a772972fcaf94e91a9f2a0f8888ea8e5
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691816B2

Reaction notes

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