5-bromo-1H-pyrrolo[2,3-b]pyridine → 5-methoxy-1H-pyrrolo[2,3-b]pyridine

HRID 1991114Notes

Reaction equation

HRID 1991114 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[N:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.[CH3:11][O:12][Na]>CN(C=O)C.[Cu]Br>[CH3:11][O:12][C:2]1[CH:3]=[C:4]2[CH:5]=[CH:6][NH:7][C:8]2=[N:9][CH:10]=1

Participants

5

Reactant 2

HCID 103079325-bromo-1H-pyrrolo[2,3-b]pyridineHCID 178418582HCID 178418582, compound

Product 1

HCID 103078715-methoxy-1H-pyrrolo[2,3-b]pyridineYield 78.3%

Reagents, catalysts & solvents 2

HCID 24593copper(I) bromideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

To 5-bromo-7-azaindole 1 (0.98 g, 5.0 mmol) in DMF (32 mL) was added 25% (w/w) MeONa (48 mL, 210 mmol) followed by copper (1) bromide (1.43 g, 10.0 mmol), and the reaction mixture was heated at 140° C. for 2.5. It was then cooled and concentrated to remove DMF. Water (100 mL) was added followed by saturated aqueous NaHCO3 (20 mL). The mixture was extracted with AcOEt (3×), the combined organic extracts dried (MgSO4) and concentrated. The solid residue was purified by SGC using AcOEt:hexane (gradient elution up to 30:70) to give 30 as a green solid (0.58 g, 78%); 1H NMR (400 MHz, CDCl3) δ 3.90 (s, 3H), 6.45 (d, J=2.3 Hz, 1H), 7.33 (d, J=2.8 Hz, 1H), 7.48 (d, J=2.2 Hz, 1H), 8.00-8.20 (bs, 1H); 10.60-10.80 (bs, NH).

Workup

  1. temperatureIt was then cooled
  2. concentrationconcentrated
  3. customto remove DMF
  4. additionWater (100 mL) was added
  5. extractionThe mixture was extracted with AcOEt (3×)
  6. dry with materialthe combined organic extracts dried (MgSO4)
  7. concentrationconcentrated
  8. customThe solid residue was purified by SGC

Sources & evidence

ORD record
ord-2a53975bcd4a40e8ba45153f3751f092
Source dataset
uspto-grants-2010_01
Patent number
US07645769B2

Reaction notes

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