Cesium carbonate → HCID 11261955, compound

HRID 568194Notes

Reaction equation

HRID 568194 reaction equation
Br/[C:2](=[CH:10]\[C:11]1[C:19]2[C:14](=[CH:15][C:16]([Cl:21])=[CH:17][C:18]=2[Cl:20])[N:13]([S:22]([C:25]2[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=2)(=[O:24])=[O:23])[C:12]=1[C:32]([O:34][CH2:35][CH3:36])=[O:33])/[C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[O:37]1[CH:41]=[CH:40][CH:39]=[C:38]1B(O)O.C(=O)([O-])[O-].[Cs+].[Cs+].C(OCC)C.CCCCCC>C1(C)C=CC=CC=1>[O:37]1[CH:41]=[CH:40][CH:39]=[C:38]1/[C:2](=[CH:10]\[C:11]1[C:19]2[C:14](=[CH:15][C:16]([Cl:21])=[CH:17][C:18]=2[Cl:20])[N:13]([S:22]([C:25]2[CH:26]=[CH:27][C:28]([CH3:31])=[CH:29][CH:30]=2)(=[O:24])=[O:23])[C:12]=1[C:32]([O:34][CH2:35][CH3:36])=[O:33])/[C:3]([O:5][C:6]([CH3:8])([CH3:7])[CH3:9])=[O:4]

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 2734357Furan-2-boronic acidHCID 11157837HCID 11157837, compoundHCID 21584099Diethylether hexane

Product 1

HCID 11261955HCID 11261955, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

Combine (Z)-2-bromo-3-(1-p-toluenesulfonyl-2-carboethoxy-4,6-dichloroindol-3-yl)propenoic acid, t-butyl ester (1.00 g, 1.6 mmol), furan-2-boronic acid (0.27 g, 2.4 mmol), and cesium carbonate (1.00 g, 3.2 mmol) in toluene (15 mL). Sparge with nitrogen for 15 minutes. Add tetrakis(triphenylphosphine)palladium(0) (50 mg). Heat to 90° C. After 3 days, partition the reaction mixture between ethyl acetate and water. Separate the layers. Dry the organic layer over MgSO4, filter, and evaporate in vacuo to give a reside. Chromatograph the residue on silica gel eluting with 15% diethyl ether/hexane to give the title compound.

Workup

  1. customSparge with nitrogen for 15 minutes
  2. custompartition the reaction mixture between ethyl acetate and water
  3. customSeparate the layers
  4. dry with materialDry the organic layer over MgSO4
  5. filtrationfilter
  6. customevaporate in vacuo
  7. customto give a reside

Sources & evidence

ORD record
ord-a7de120200494c918a2d9cec2e1ac94a
Source dataset
uspto-grants-2001_01
Patent number
US06180786B2

Reaction notes

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