Water → HCID 86616467, compound

HRID 1864787Notes

Reaction equation

HRID 1864787 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6](B(O)O)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.Br[C:14]1[CH:15]=[C:16]([CH:20]=[O:21])[CH:17]=[N:18][CH:19]=1.C(Cl)Cl.C(=O)([O-])[O-].[Na+].[Na+].O>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].O1CCOCC1>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:14]3[CH:15]=[C:16]([CH:20]=[O:21])[CH:17]=[N:18][CH:19]=3)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

8

Reactant 5

HCID 962WaterHCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 27343615-Indolylboronic acidHCID 27847345-Bromo-3-pyridinecarboxaldehyde

Product 1

HCID 86616467HCID 86616467, compoundYield 62.6%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
100 °C

Procedure

Indole-5-boronic acid (1 g 6.25 mmol), 5-bromopyridine-3-carboxaldehyde (1.3 g, 6.9 mmol) and PdCl2(dppf).DCM (2.2 g, 2.7 mmol) and 15 ml of dioxane were evenly distributed amongst five 5 mL microwave vessels (Smith Personal Chemistry). The mixtures were degassed (evacuate in vacuo and pressurize with nitrogen). Sodium carbonate in water (2M, 9.38 mL, 18.7 mmol) was evenly distributed amongst the reaction vessels and the mixtures degassed two more times as described above. The mixture was heated to 100° C. for 12 min in a Smith synthesizer. The samples were cooled, combined and washed with water. The aqueous phase was extracted with dichloromethane and the combined organic phases were dried over MgSO4, filtered and evaporated to give crude product. Chromatography (elution with ethyl acetate/cyclohexane) provided 870 mg of product.

Workup

  1. customThe mixtures were degassed
  2. custom(evacuate in vacuo and pressurize with nitrogen)
  3. customthe mixtures degassed two more times
  4. temperatureThe samples were cooled
  5. washwashed with water
  6. extractionThe aqueous phase was extracted with dichloromethane
  7. dry with materialthe combined organic phases were dried over MgSO4
  8. filtrationfiltered
  9. customevaporated
  10. customto give crude product
  11. washChromatography (elution with ethyl acetate/cyclohexane)

Sources & evidence

ORD record
ord-ab2325341edd46ab8fabefc734a8b9f3
Source dataset
uspto-grants-2009_12
Patent number
US07625889B2

Reaction notes

Loading…