Sodium Carbonate → HCID 57537528, compound

HRID 1693713Notes

Reaction equation

HRID 1693713 reaction equation
[Br:1][C:2]1[C:3]([Cl:20])=[C:4]2[C:10](I)=[CH:9][N:8]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[C:5]2=[N:6][CH:7]=1.[C:21]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1B(O)O)([CH3:24])([CH3:23])[CH3:22].C(=O)([O-])[O-].[Na+].[Na+].S([O-])([O-])(=O)=O.[Na+].[Na+]>C(#N)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[Br:1][C:2]1[C:3]([Cl:20])=[C:4]2[C:10]([C:32]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[CH2:26][O:25][C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:9][N:8]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[C:5]2=[N:6][CH:7]=1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 24436Sodium SulfateHCID 37967282-(tert-Butoxymethyl)phenylboronic acidHCID 57537477HCID 57537477, compound

Product 1

HCID 57537528HCID 57537528, compoundYield 12%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

5-Bromo-4-chloro-3-iodo-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridine (500 mg, 1.02 mmol), 2-(tert-Butoxymethyl)phenylboronic acid (224 mg, 1.05 mmol), dichlorobis(triphenylphosphine)palladium(II) (42 mg, 0.05 mmol), and 1 mL of sodium carbonate solution (2M, 2 mmol) were dissolved in 5 mL of acetonitrile and 5 mL of THF under an atmosphere of nitrogen. The mixture was heated at 60° C. with rapid stirring under N2 for 2 h. Sodium sulfate was added to the reaction mixture and the slurry was filtered over Celite and concentrated. The crude product was purified by flash silica gel chromatography using a gradient of ethyl acetate in hexanes to afford the title compound (66 mg, 0.12 mmol, 12% yield).

Workup

  1. filtrationthe slurry was filtered over Celite
  2. concentrationconcentrated
  3. customThe crude product was purified by flash silica gel chromatography

Sources & evidence

ORD record
ord-249d910ca48c42389905f5a2ece898ce
Source dataset
uspto-grants-2012_04
Patent number
US08158647B2

Reaction notes

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