Cesium carbonate → HCID 58368636, compound

HRID 1192621Notes

Reaction equation

FC(F)(F)S(O[C:7]1[C:8]([C:18](=[O:20])[CH3:19])=[CH:9][C:10]([Cl:17])=[C:11]2[C:16]=1[N:15]=[CH:14][CH:13]=[CH:12]2)(=O)=O.[N:23]1([CH:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCCC1.ClCCl.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[N:23]1([CH:29]2[CH2:34][CH2:33][N:32]([C:7]3[C:8]([C:18](=[O:20])[CH3:19])=[CH:9][C:10]([Cl:17])=[C:11]4[C:16]=3[N:15]=[CH:14][CH:13]=[CH:12]4)[CH2:31][CH2:30]2)[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

Conditions

Temperature: 65 °C

Procedure

A stirred mixture of 7-acetyl-5-chloroquinolin-8-yl trifluoromethanesulfonate (0.14 g, 0.40 mmol, from Example 47, Step 2), 1,4′-bipiperidine (0.0799 g, 0.475 mmol), palladium acetate (1.8 mg, 0.0080 mmol), (S)-(−)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (7.4 mg, 0.012 mmol), and cesium carbonate (0.361 g, 1.11 mmol) in tetrahydrofuran (3 mL) was heated at 65° C. overnight. The mixture was cooled, diluted with dichloromethane and filtered. The filtrate was washed with brine, dried over MgSO4 and evaporated. The resulting residue was purified on silica gel (eluting with 0 to 10% methanol in dichloromethane) to give the desired product (16.5 mg, 11%). LCMS calculated for C21H27ClN3O (M+H)+: m/z=372.2; Found: 372.1.

Workup

temperatureThe mixture was cooled
filtrationfiltered
washThe filtrate was washed with brine
dry with materialdried over MgSO4
customevaporated
customThe resulting residue was purified on silica gel (eluting with 0 to 10% methanol in dichloromethane)

Sources & evidence

ORD record: ord-9e2aba787cd943f795584bf5ff690621
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08680108B2

Reaction notes

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