Cesium carbonate → HCID 10321773, compound

HRID 1987031Notes

Reaction equation

HRID 1987031 reaction equation
FC(F)(F)S(O[C:7]1[CH:16]=[C:15]2[C:10]([CH:11]=[CH:12][C:13](=[O:24])[N:14]2[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[Cl:23])=[C:9]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[Cl:31])[CH:8]=1)(=O)=O.[NH2:34][CH:35]([CH2:38][OH:39])[CH2:36][OH:37].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(Cl)(Cl)Cl.O>[Cl:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[N:14]1[C:15]2[C:10](=[C:9]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[Cl:31])[CH:8]=[C:7]([NH:34][CH:35]([CH2:38][OH:39])[CH2:36][OH:37])[CH:16]=2)[CH:11]=[CH:12][C:13]1=[O:24]

Participants

9

Reactant 4

HCID 10796Cesium carbonateHCID 68294SerinolHCID 634876Binap, (A+-)-HCID 57722974HCID 57722974, compound

Product 1

HCID 10321773HCID 10321773, compoundYield 16%

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 6212ChloroformSolventHCID 312751,4-DioxaneSolvent

Procedure

1,5-bis(2-chlorophenyl)-2-oxo-1,2-dihydro-7-quinolinyl trifluoromethanesulfonate (50 mg, 0.097 mmol), serinol (44 mg, 0.483 mmol), racemic BINAP (74 mg, 0.19 mmol), palladium(II) acetate (17 mg, 0.076 mmol), and cesium carbonate (0.14 g, 0.43 mmol) in 1,4-dioxan (2 ml) were heated in a Smith creator microwave at 130° for 15 min. Water (3 ml) and chloroform (4 ml) were added to the reaction mixture, which was then passed through a hydrophobic frit, and blown down under a stream of nitrogen. The residue was purified by mass directed autoprep to afford the title compound as a gum (7 mg, 16%).

Workup

  1. customThe residue was purified by mass

Sources & evidence

ORD record
ord-7d89dba0ba0041fead14ea5244ad50a8
Source dataset
uspto-grants-2009_06
Patent number
US07550480B2

Reaction notes

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