Water → 5-chloro-8-(2-fluorophenyl)-N-methoxy-N-methylquinoline-7-carboxamide

HRID 1192488Notes

Reaction equation

FC(F)(F)S(O[C:7]1[C:8]([C:18]([N:20]([O:22][CH3:23])[CH3:21])=[O:19])=[CH:9][C:10]([Cl:17])=[C:11]2[C:16]=1[N:15]=[CH:14][CH:13]=[CH:12]2)(=O)=O.[F:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1B(O)O.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>[Cl:17][C:10]1[CH:9]=[C:8]([C:18]([N:20]([O:22][CH3:23])[CH3:21])=[O:19])[C:7]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=2[F:26])=[C:16]2[C:11]=1[CH:12]=[CH:13][CH:14]=[N:15]2

Participants

Conditions

Temperature: 100 °C

Procedure

To a mixture of 5-chloro-7-{[methoxy(methyl)amino]carbonyl}quinolin-8-yl trifluoromethanesulfonate (0.16 g, 0.41 mmol) and (2-fluorophenyl)boronic acid (0.069 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 then concentrated. The residue was purified on silica gel (eluting with 0-60% EtOAc in Hexane) to give the desired compound as a bis-trifluoroacetate salt (42 mg, 29%). LCMS calculated for C18H15ClFN2O2(M+H)+: m/z=345.1; found: 345.0.

Workup

temperatureAfter cooling
washwashed with water
dry with materialdried over MgSO4
concentrationconcentrated
customThe residue was purified on silica gel (eluting with 0-60% EtOAc in Hexane)

Sources & evidence

ORD record: ord-f0843e002fac482aa6d4e159a4ad9e64
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08680108B2

Reaction notes

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