Cesium carbonate → HCID 66771868, compound

HRID 1645285Notes

Reaction equation

HRID 1645285 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+].CC1(C)C(C)(C)OB([C:33]2[CH:34]=[C:35]([CH:45]=[CH:46][CH:47]=2)[O:36][CH2:37][CH2:38][N:39]2[CH2:44][CH2:43][O:42][CH2:41][CH2:40]2)O1>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:46]2[CH:47]=[CH:33][CH:34]=[C:35]([O:36][CH2:37][CH2:38][N:39]3[CH2:40][CH2:41][O:42][CH2:43][CH2:44]3)[CH:45]=2)=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 467390854-{2-[3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]ethyl}morpholineHCID 667728293-((5-Bromofuran-2-yl)methylene)-5-chloroindolin-2-one

Product 1

HCID 66771868HCID 66771868, compound

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

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 4-(2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)ethyl)morpholine (62 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-(3-(2-morpholinoethoxy)phenyl)furan-2-yl)methylene)indolin-2-one. LCMS (M+1=451).

Workup

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

Sources & evidence

ORD record
ord-8bd17a996b3049ec9b095738e3608cf0
Source dataset
uspto-grants-2012_02
Patent number
US08124649B2

Reaction notes

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