Cesium carbonate → 5-Chloro-3-((5-(6-(dimethylamino)pyridin-3-yl)furan-2-yl)methylene)indolin-2-one

HRID 1645289Notes

Reaction equation

Br[C:2]1[O:6][C:5]([CH:7]=[C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([Cl:17])[CH:15]=3)[NH:10][C:9]2=[O:18])=[CH:4][CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].[CH3:25][N:26]([CH3:36])[C:27]1[N:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=1>O1CCOCC1.O>[Cl:17][C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:18])[C:8]2=[CH:7][C:5]1[O:6][C:2]([C:30]2[CH:31]=[N:32][C:27]([N:26]([CH3:36])[CH3:25])=[CH:28][CH:29]=2)=[CH:3][CH:4]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To 3-((5-bromofuran-2-yl)methylene)-5-chloroindolin-2-one (50 mg, 0.155 mmol) in dioxane/water (5% water) was added Cs2CO3 (152 mg, 0.466 mmol) and 6-(dimethylamino)pyridin-3-ylboronic acid (34 mg, 0.186 mmol). The mixture was degassed with nitrogen for 5 minutes then heated in microwave for 20 minutes at 120° C. The solution was diluted with water and the solid formed was isolated by filtration. The solid was purified by HPLC to yield 5-chloro-3-((5-(6-(dimethylamino)pyridin-3-yl)furan-2-yl)methylene)indolin-2-one. LCMS (M+1=366).

Workup

customThe mixture was degassed with nitrogen for 5 minutes
additionThe solution was diluted with water
customthe solid formed
customwas isolated by filtration
customThe solid was purified by HPLC

Sources & evidence

ORD record: ord-86529ec499d74fcda2d8f0bba69c533e
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08124649B2

Reaction notes

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