Potassium Carbonate → 4-chloro-2-phenyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridine

HRID 1851092Notes

Reaction equation

HRID 1851092 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[C:9](I)=[CH:10][C:3]=12.[C:20]1(B(O)O)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[C:9]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:10][C:3]=12

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 587990714-Chloro-2-iodo-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 583683444-chloro-2-phenyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridineYield 63.4%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

4-Chloro-2-iodo-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridine (329 mg, 0.805 mmol) and phenylboronic acid (118 mg, 0.966 mmol) were dissolved in dioxane and then Pd(PPh3)4 (46 mg, 0.04 mmol) was added. After adding 1 M potassium carbonate aqueous solution (1.61 mL), the resulting reaction mixture was stirred at 80° C. for 2 hours. The reaction mixture was extracted with dichloromethane and water. The organic layer was washed with sodium chloride aqueous solution, dried with magnesium sulfate, and then filtered. The filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=9:1) to give the target compound as a yellow oil (182 mg, 0.51 mmol, 63% yield).

Workup

  1. customthe resulting reaction mixture
  2. extractionThe reaction mixture was extracted with dichloromethane and water
  3. washThe organic layer was washed with sodium chloride aqueous solution
  4. dry with materialdried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-1f1e8aff73ab4496bc8e626b8656d84e
Source dataset
uspto-grants-2015_02
Patent number
US08957102B2

Reaction notes

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