Cesium carbonate → 1-(2-(4-(2-Fluoro-4-(1-(phenylcarbamoyl)cyclopropanecarboxamido)phenoxy)quinolin-7-yloxy)ethyl)cyclopropyl benzoate

HRID 1517916Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([N:20](C2C=CC=CC=2)[C:21]([C:23]2(C(N)=O)[CH2:25][CH2:24]2)=[O:22])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[C:18]2[C:13](=[CH:14][C:15](O)=[CH:16][CH:17]=2)[N:12]=[CH:11][CH:10]=1.CS([O:39][CH2:40][CH2:41][C:42]1([O:45][C:46](=[O:53])[C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[CH2:44][CH2:43]1)(=O)=O.[C:54]([O-:57])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[C:46]([O:45][C:42]1([CH2:41][CH2:40][O:39][C:15]2[CH:14]=[C:13]3[C:18]([C:9]([O:8][C:7]4[CH:6]=[CH:5][C:4]([NH:20][C:21]([C:23]5([C:54](=[O:57])[NH:12][C:13]6[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=6)[CH2:24][CH2:25]5)=[O:22])=[CH:3][C:2]=4[F:1])=[CH:10][CH:11]=[N:12]3)=[CH:17][CH:16]=2)[CH2:44][CH2:43]1)(=[O:53])[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a mixture of N-(3-fluoro-4-(7-hydroxyquinolin-4-yloxy)phenyl)-N-phenylcyclo-propane-1,1-dicarboxamide (91 mg, 0.2 mmol) and 2-(1-(benzoyloxy)cyclopropyl)ethyl methanesulfonate (113.6 mg, 0.4 mmol) in DMF (3 mL) were added Cs2CO3 (195 mg, 0.6 mmol, Aladdin). The reaction was stirred at 50° C. overnight. The solvent was then removed in vacuo, and the residue was extracted with CHCl3 (30 mL). The organic layer was dried over Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (EtOAc) to afford the title compound as a light yellow solid (75 mg, 58%).

Workup

customThe solvent was then removed in vacuo
extractionthe residue was extracted with CHCl3 (30 mL)
dry with materialThe organic layer was dried over Na2SO4
concentrationconcentrated in vacuo
customThe residue was purified by a silica gel column chromatography (EtOAc)

Sources & evidence

ORD record: ord-f50208537b2c4382bfd4ead69f668827
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08232294B2

Reaction notes

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