Water → HCID 57537631, compound

HRID 1693702Notes

Reaction equation

HRID 1693702 reaction equation
[Br:1][C:2]1[C:3](I)=[C:4]2[CH:10]=[CH:9][N:8]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[C:5]2=[N:6][CH:7]=1.[CH3:20][Zn]C.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C.C(OCC)(=O)C>[Br:1][C:2]1[C:3]([CH3:20])=[C:4]2[CH:10]=[CH:9][N:8]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[C:5]2=[N:6][CH:7]=1

Participants

8

Reactant 4

HCID 962WaterHCID 24436Sodium SulfateHCID 57537463HCID 57537463, compoundHCID 178477796HCID 178477796, compound

Product 1

HCID 57537631HCID 57537631, compoundYield 81%

Reagents, catalysts & solvents 3

HCID 178418851HCID 178418851, compoundCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
23 °C

Procedure

5-Bromo-4-iodo-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridine (1.00 g, 2.21 mmol) and bis(tri-t-butylphosphine)palladium(0) (56 mg, 0.110 mmol) were combined and dissolved in anhydrous tetrahydrofuran (20 mL) in an oven-dried round-bottom flask. Dimethylzinc (552 μL, 1.11 mmol, 2.0 M solution in tetrahydrofuran). The solution was allowed to stir at 23° C. for 1 hour. To the mixture was added water (50 mL) followed by ethyl acetate (50 mL). Layers were mixed well, and the organic layer was stirred over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by flash silica gel chromatography using a gradient of ethyl acetate in hexanes to afford 5-Bromo-4-methyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridine (307 mg, 0.899 mmol, 41%) as a brown oil. 1H-NMR [500 MHz, d6-DMSO]: 8.43 (s, 1H), 7.71 (d, 1H), 6.79 (d, 1H), 5.69 (s, 1H), 3.61 (t, 2H), 2.66 (s, 3H), 0.93 (t, 2H), 0.0 (s, 9H); MS [MH+] m/z: 341.1, 343.0

Workup

  1. additionLayers were mixed well
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by flash silica gel chromatography

Sources & evidence

ORD record
ord-3977d3025e034134999809b7f7756363
Source dataset
uspto-grants-2012_04
Patent number
US08158647B2

Reaction notes

Loading…