Cesium carbonate → HCID 86703367, compound

HRID 1411161Notes

Reaction equation

HRID 1411161 reaction equation
ClC1C(OC2C=CN=C(Cl)C=2)=CC(F)=C([NH:8][C:9]([C:11]2[C:12](=[O:27])[N:13]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[CH:14]=[CH:15][C:16]=2[O:17][CH2:18][CH3:19])=[O:10])C=1.C1(C(N)=O)CC1.C([O-])([O-])=O.[Cs+].[Cs+].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[CH2:18]([O:17][C:16]1[CH:15]=[CH:14][N:13]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)[C:12](=[O:27])[C:11]=1[C:9]([NH2:8])=[O:10])[CH3:19]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 80376CyclopropanecarboxamideHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 86703366HCID 86703366, compound

Product 1

HCID 86703367HCID 86703367, compoundYield 104%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

Using the procedure of Example 12, N-(5-chloro-4-((2-chloropyridin-4-yl)oxy)-2-fluorophenyl)-4-ethoxy-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxamide (0.05 g, 0.094 mmol), cyclopropancarboxamide (12 mg, 0.14 mmol), Cs2CO3 (0.05 g, 0.14 mmol), Xantphos (6 mg, 0.010 mmol), Pd2(dba)3 (5 mg, 0.005 mmol) and dioxane (2 mL) were combined to obtain N-(5-chloro-4-(2-(cyclopropanecarboxamido)pyridin-4-yl)oxy)-2-fluorophenyl)-4-ethoxy-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxamide (27 mg, 48.4% yield). 1H NMR (400 MHz, DMSO-d6): δ 11.20 (s, 1H), 10.88 (s, 1H), 8.50 (d, J=7.8 Hz, 1H), 8.19 (d, J=5.7 Hz, 1H), 7.92 (d, J=7.8 Hz, 1H), 7.59 (d, J=2.4 Hz, 1H), 7.50 (m, 3H), 7.36 (t, J=8.7 Hz, 2H), 6.68 (dd, J=5.7, 2.4 Hz, 1H), 6.55 (d, J=7.9 Hz, 1H), 4.28 (q, J=7.0 Hz, 2H), 1.95 (m, 1H), 1.33 (t, J=7.0 Hz, 3H), 0.76 (t, J=5.9 Hz, 4H); MS (ESI) m/z: 581.1 (M+H+).

Sources & evidence

ORD record
ord-57b78423f60b4e289d2bb11d2d174c76
Source dataset
uspto-grants-2014_12
Patent number
US08921565B2

Reaction notes

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