Cesium carbonate → ethyl 5-chloro-6-(2,3-dihydro-1H-inden-2-ylamino)nicotinate

HRID 226463Notes

Reaction equation

C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:47][C:48]1[C:49](Cl)=[N:50][CH:51]=[C:52]([CH:58]=1)[C:53]([O:55][CH2:56][CH3:57])=[O:54].[NH2:60][CH:61]1[CH2:69][C:68]2[C:63](=[CH:64][CH:65]=[CH:66][CH:67]=2)[CH2:62]1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[Cl:47][C:48]1[C:49]([NH:60][CH:61]2[CH2:69][C:68]3[C:63](=[CH:64][CH:65]=[CH:66][CH:67]=3)[CH2:62]2)=[N:50][CH:51]=[C:52]([CH:58]=1)[C:53]([O:55][CH2:56][CH3:57])=[O:54]

Participants

Conditions

Temperature: 10 °C

Procedure

Palladium(II) acetate (25 mg) and 2,2′-bis(diphenylphosphino)-1,1′-binaphthalene (106 mg) in dioxane (10 mL) was stirred at ambient temperature for 15 minutes. To this suspension was added ethyl 5,6-dichloronicotinate (500 mg), 2-aminoindane (363 mg), and cesium carbonate (1.1 g), and the mixture was heated at 10° C. for 8 hours. The resulting mixture was allowed to cool to ambient temperature, poured into water, and extracted with ethyl acetate. The organic phase was washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1 v/v) to give ethyl 5-chloro-6-(2,3-dihydro-1H-inden-2-ylamino)nicotinate (420 mg) as a pale tan solid.

Workup

temperatureto cool to ambient temperature
extractionextracted with ethyl acetate
washThe organic phase was washed with brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated in vacuo
customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1 v/v)

Sources & evidence

ORD record: ord-bad172f9d02e4b9bb17bb1df882e4187
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07557127B2

Reaction notes

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