Cesium carbonate → HCID 67072816, compound

HRID 1925567Notes

Reaction equation

HRID 1925567 reaction equation
I[C:2]1[C:10]2[N:9]3[CH:11]=[CH:12][CH:13]=[C:8]3[C:7](=[O:14])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[N:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[C:17](B(O)O)[CH:16]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd]>[N:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[C:17]([C:2]2[C:10]3[N:9]4[CH:11]=[CH:12][CH:13]=[C:8]4[C:7](=[O:14])[C:6]=3[CH:5]=[CH:4][CH:3]=2)[CH:16]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 2734663Quinoline-3-boronic acidHCID 58369284HCID 58369284, compound

Product 1

HCID 67072816HCID 67072816, compoundYield 63.7%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
123 °C

Procedure

In a 100 ml round-bottomed flask under argon, a mixture of 361 mg of 5-iodopyrrolo[1,2-a]indol-9-one (which can be prepared according to J. Med. Chem. 2004, 47(6), 1448), 214 mg of 3-quinolineboronic acid, 603 mg of caesium carbonate and 143 mg of tetrakis(triphenylphosphine)palladium(O) in 20 ml of dimethylformamide is heated at 123° C. After 3 hours, the reaction medium is evaporated to dryness under vacuum and the residue is taken up in ethyl acetate and filtered. The filtrate is washed with water, twice with a saturated solution of sodium bicarbonate and then with a saturated solution of sodium chloride, dried with magnesium sulphate, and evaporated to dryness under vacuum. The residue is chromatographed on silica gel (15-40 μm), elution being carried out with a gradient of ethyl acetate (20% to 30% v/v) in n-heptane. 231 mg of 5-quinolin-3-ylpyrrolo[1,2-a]indol-9-one are obtained in the form of a solid, the characteristics of which are the following:

Workup

  1. customthe reaction medium is evaporated to dryness under vacuum
  2. filtrationfiltered
  3. washThe filtrate is washed with water, twice with a saturated solution of sodium bicarbonate
  4. dry with materialwith a saturated solution of sodium chloride, dried with magnesium sulphate
  5. customevaporated to dryness under vacuum
  6. customThe residue is chromatographed on silica gel (15-40 μm), elution

Sources & evidence

ORD record
ord-204f34e8640c4faea030327c7ac07ddd
Source dataset
uspto-grants-2012_05
Patent number
US08178687B2

Reaction notes

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