Cesium carbonate → HCID 86641407, compound

HRID 1512189Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:10]=[C:11]([C:19]([O:21][CH3:22])=[O:20])[C:12]3[C:17]([CH:18]=2)=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:5]=[CH:4][N:3]=1.[CH:23]1([C:26]([NH2:28])=[O:27])[CH2:25][CH2:24]1.C([O-])([O-])=O.[Cs+].[Cs+].[NH4+].[Cl-]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH:23]1([C:26]([NH:28][C:2]2[CH:7]=[C:6]([O:8][C:9]3[CH:10]=[C:11]([C:19]([O:21][CH3:22])=[O:20])[C:12]4[C:17]([CH:18]=3)=[CH:16][CH:15]=[CH:14][CH:13]=4)[CH:5]=[CH:4][N:3]=2)=[O:27])[CH2:25][CH2:24]1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 3-[[2-chloro-4-pyridinyl]oxy]-1-naphthalenecarboxylic acid, methyl ester (0.188 g, 0.60 mmol), cyclopropanecarboxamide (0.077 g, 0.90 mmol), Cs2CO3 (0.274 g, 0.84 mmol), 1,1′-(9,9-dimethyl-9H-xanthene-4,5-diyl)bis[1,1-diphenylphosphine (0.035 g, 0.06 mmol; xantphos; Aldrich) and Pd2(dba)3 (0.018 g, 0.020 mmol) in dioxane (6 mL) is stirred at 90° C. for 16 h under an argon atmosphere. The cooled mixture is treated with saturated aqueous NH4Cl (50 mL) and extracted with ethyl acetate. The combined extracts are washed (brine), dried (Na2SO4) and the solvent is evaporated off under reduced pressure to give a crude product, which is purified by column chromatography (SiO2; ethylacetate/hexane 1:1) to afford the title compound as a viscous oil.

Workup

extractionextracted with ethyl acetate
washThe combined extracts are washed (brine)
dry with materialdried (Na2SO4)
customthe solvent is evaporated off under reduced pressure
customto give a crude product, which
customis purified by column chromatography (SiO2; ethylacetate/hexane 1:1)

Sources & evidence

ORD record: ord-29fee89370b1497e904712a9f86ac716
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08217045B2

Reaction notes

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