Cesium carbonate → HCID 58503960, compound

HRID 2407736Notes

Reaction equation

Cl[C:2]1[CH:3]=[C:4]([CH:10]=[C:11]([O:13][CH2:14][CH3:15])[N:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].[C:16]1([C:22]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[NH:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[Cs+].[Cs+].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>C1(C)C=CC=CC=1.C(OCC)(=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:16]1([C:22](=[N:23][C:2]2[CH:3]=[C:4]([CH:10]=[C:11]([O:13][CH2:14][CH3:15])[N:12]=2)[C:5]([O:7][CH2:8][CH3:9])=[O:6])[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 110 °C

Procedure

The compound prepared in Example 229 (0.26 g), diphenylmethanimine (0.24 g), cesium carbonate (1.8 g), racemic-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (0.070 g) and Pd(OAc)2 (0.013 g) were dissolved in degassed toluene (4.5 mL) and then heated under argon at 110° C. for 1 hr. The reaction was cooled, diluted with ethyl acetate and filtered through celite (trade mark) with an ethyl acetate wash. The combined organic solutions were purified by column chromatography using an eluant of 0-2% ethyl acetate/dichloromethane to provide the title compound (0.40 g) with the following physical data.

Workup

temperatureThe reaction was cooled
filtrationfiltered through celite (trade mark) with an ethyl acetate
washwash
customThe combined organic solutions were purified by column chromatography

Sources & evidence

ORD record: ord-c1ba114e411b4d0584598573a201ed32
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08809538B2

Reaction notes

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