Dichloromethane → HCID 68749773, compound

HRID 1864806Notes

Reaction equation

HRID 1864806 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[N:10][CH:9]=[C:8](Cl)[N:7]=1)=[O:5])[CH3:2].[NH:13]1[C:21]2[C:16](=[CH:17][C:18](B(O)O)=[CH:19][CH:20]=2)[CH:15]=[CH:14]1.C(=O)([O-])[O-].[Cs+].[Cs+].C(Cl)Cl>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[N:10][CH:9]=[C:8]([C:18]2[CH:17]=[C:16]3[C:21](=[CH:20][CH:19]=2)[NH:13][CH:14]=[CH:15]3)[N:7]=1)=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 10796Cesium carbonateHCID 27343615-Indolylboronic acidHCID 19084590Ethyl 6-chloropyrazine-2-carboxylate

Product 1

HCID 68749773HCID 68749773, compoundYield 55.4%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
85 °C

Procedure

6-Chloro-pyrazine-2-carboxylic acid ethyl ester (1.35 g, 7.23 mmol) was added to indole-5-boronic acid (1.16 g, 7.23 mmol), cesium carbonate (9.43 g, 28.9 mmol) and PdCl2(dppf).DCM (591 mg, 0.72 mmol) in 30 mL of dioxane. The mixture was degassed (evacuate in vacuo and pressurize with nitrogen), 14.5 mL of water was added and the mixture degassed. The mixture was heated at 85° C. for 2.5 h. and the mixture was allowed to cool and the layers were separated. The aqueous phase was extracted with chloroform and the combined organic layers were washed with brine, dried over sodium sulfate, filtered and evaporated. Chromatography of the residue on silica gel, eluting with ethyl acetate/pentane afforded 1.07 g of product. LC/MS: Retention time, 3.21 min; (M+H)=268.1.

Workup

  1. customThe mixture was degassed
  2. custom(evacuate in vacuo and pressurize with nitrogen), 14.5 mL of water
  3. additionwas added
  4. customthe mixture degassed
  5. temperatureto cool
  6. customthe layers were separated
  7. extractionThe aqueous phase was extracted with chloroform
  8. washthe combined organic layers were washed with brine
  9. dry with materialdried over sodium sulfate
  10. filtrationfiltered
  11. customevaporated
  12. washChromatography of the residue on silica gel, eluting with ethyl acetate/pentane

Sources & evidence

ORD record
ord-dd9d542dd3244bb5a664ba1a8594b052
Source dataset
uspto-grants-2009_12
Patent number
US07625889B2

Reaction notes

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