Sodium Carbonate → HCID 57537472, compound

HRID 1693712Notes

Reaction equation

HRID 1693712 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.[CH3:21][O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1B(O)O.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:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=3[O:22][CH3:21])=[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 27339582-Methoxyphenylboronic acidHCID 57537477HCID 57537477, compound

Product 1

HCID 57537472HCID 57537472, compoundYield 51%

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 (916 mg, 2 mmol), 2-methoxyphenyl boronic acid (321 mg, 2.2 mmol), dichlorobis(triphenylphosphine)palladium(II) (74 mg, 0.1 mmol), and 2 mL of 2M Na2CO3 (aq) were dissolved in 10 mL of acetonitrile and 10 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 (452 mg, 1.02 mmol, 51% yield). 1H NMR (500 MHz, DMSO-d6) δ 8.50 (s, 1H), 7.74 (s, 1H), 7.37 (m, 1H), 7.23 (dd, J=7.5 Hz, J2=1.5 Hz, 1H), 7.05 (dd, J=8 Hz, J2=1 Hz, 1H), 6.98 (td, J=7.5 Hz, J2=1 Hz, 1H), 5.63 (s, 2H), 3.67 (s, 3H), 3.56 (t, J=8 Hz, 2H), 0.82 (t, J=8 Hz, 2H), −0.09 (s, 9H). MS: m/z 467.1/469.1 (M+H+).

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-94680ed6fae3407baac0feceee753b56
Source dataset
uspto-grants-2012_04
Patent number
US08158647B2

Reaction notes

Loading…