Potassium Carbonate → HCID 59494553, compound

HRID 872040Notes

Reaction equation

HRID 872040 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].CB1OB(C)OB(C)O1.Cl[C:17]1[N:22]=[C:21]2[N:23]([C:26]([O:28][CH3:29])=[O:27])[CH:24]=[CH:25][C:20]2=[CH:19][CH:18]=1>O1CCOCC1.Cl[Pd]Cl.C1(P([C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH3:1][C:17]1[N:22]=[C:21]2[N:23]([C:26]([O:28][CH3:29])=[O:27])[CH:24]=[CH:25][C:20]2=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 574072TrimethylboroxineHCID 15013891methyl 6-chloro-1H-pyrrolo[2,3-b]pyridine-1-carboxylate

Product 1

HCID 59494553HCID 59494553, compoundYield 75%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
110 °C

Procedure

Potassium carbonate (5.03 g), trimethyl boroxin (3.18 ml) and bis(diphenylphosphino)ferrocene dichloropalladium(II) (666 mg) were added to a solution of methyl 6-chloro-1H-pyrrolo[2,3-b]pyridin-1-carboxylate (1.92 g) in 1,4-dioxane (140 ml) and the mixture was stirred at 110° C. for 4 hours under argon atmosphere. The reaction mixture was cooled to room temperature, insoluble materials were filtered and the filtrate was concentrated in vacuo. The residue was diluted with ethyl acetate, washed with water and saturated brine successively, dried over magnesium sulfate and concentrated in vacuo. The resulted residue was purified with a silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=4/1 to 3/7) to give methyl 6-methyl-1H-pyrrolo[2,3-b]pyridin-1-carboxylate (1.30 g) as a brown powder.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationinsoluble materials were filtered
  3. concentrationthe filtrate was concentrated in vacuo
  4. additionThe residue was diluted with ethyl acetate
  5. washwashed with water and saturated brine successively
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe resulted residue was purified with a silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=4/1 to 3/7)

Sources & evidence

ORD record
ord-76cf66fa987044fe88744d57f6c88b49
Source dataset
uspto-grants-2015_03
Patent number
US08975252B2

Reaction notes

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