Water → HCID 86656164, compound

HRID 1192473Notes

Reaction equation

FC(F)(F)S(O[C:7]1[C:8]([C:17]([N:19]([O:21][CH3:22])[CH3:20])=[O:18])=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]=[CH:14][CH:13]=[CH:12]2)(=O)=O.[F:25][C:26]1[CH:27]=[C:28](B(O)O)[CH:29]=[C:30]([F:32])[CH:31]=1.C(=O)([O-])[O-].[Na+].[Na+].O>O1CCOCC1.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:25][C:26]1[CH:27]=[C:28]([C:7]2[C:8]([C:17]([N:19]([O:21][CH3:22])[CH3:20])=[O:18])=[CH:9][CH:10]=[C:11]3[C:16]=2[N:15]=[CH:14][CH:13]=[CH:12]3)[CH:29]=[C:30]([F:32])[CH:31]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a mixture of 7- {[methoxy(methyl)amino]carbonyl}quinolin-8-yl trifluoromethanesulfonate (0.15 g, 0.41 mmol) and (3,5-difluorophenyl)boronic acid (0.078 g, 0.49 mmol) in 1,4-dioxane (2 mL) was added 1 N solution of sodium carbonate in water (0.62 mL, 34 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.024 g, 0.020 mmol). The mixture was heated at 100° C. overnight. After cooling, the mixture was diluted with ethyl acetate, washed with water, dried over MgSO4, and concentrated. The residue was purified on silica gel (eluting with 0-80% EtOAc in Hexane) to give the desired product (110 mg, 81.4%). LCMS calculated for C18H15F2N2O2(M+H)+: m/z=329.1; found: 329.0.

Workup

temperatureAfter cooling
washwashed with water
dry with materialdried over MgSO4
concentrationconcentrated
customThe residue was purified on silica gel (eluting with 0-80% EtOAc in Hexane)

Sources & evidence

ORD record: ord-646de4f1d05b4b0782afa8981c801b94
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08680108B2

Reaction notes

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