Iodine → 2-Iodo-4-methoxy-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

HRID 1020907Notes

Reaction equation

HRID 1020907 reaction equation
[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[CH:17][C:18]([O:19][CH3:20])=[C:13]3[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li]CCCC.[I:26]I.[O-]S([O-])(=S)=O.[Na+].[Na+]>C1COCC1.C(OCC)(=O)C.O>[C:1]1([S:7]([N:10]2[C:14]3[C:13](=[C:18]([O:19][CH3:20])[CH:17]=[CH:16][N:15]=3)[CH:12]=[C:11]2[I:26])(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

8

Reactant 4

HCID 807IodineHCID 24477Sodium ThiosulfateHCID 49758931HCID 49758931, compoundHCID 178418339Butyllithium

Product 1

HCID 672735222-Iodo-4-methoxy-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridineYield 69.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1-benzenesulfonyl-4-methoxy-1H-pyrrolo[2,3-b]pyridine (1.0 g, 3.47 mmol) in THF (50 mL) cooled in a dry ice-acetone bath was added n-BuLi (2.1M in hexanes, 2.0 mL). The mixture was stirred for 20 minutes, warmed to 0° C. and stirred for an additional 30 minutes, then cooled to −78° C. A solution of iodine (1.06 g, 4.16 mmol) in THF (10 mL) was added dropwise over 5 minutes and the mixture was warmed to 0° C. and stirred for one hour. Water (10 mL) was added followed by 10% aq. Na2S2O3 (10 mL) and stirred for 5 minutes. Ethyl acetate (50 mL) was added and the organic phase was washed with water, saturated aqueous sodium bicarbonate and brine, dried (MgSO4), filtered and concentrated to afford 1.0 g of 1-benzenesulfonyl-2-iodo-4-methoxy-7-azaindole as a yellow solid which was carried forward without further purification. MS m/z 415.

Workup

  1. stirringstirred for an additional 30 minutes
  2. temperaturecooled to −78° C
  3. temperaturethe mixture was warmed to 0° C.
  4. stirringstirred for one hour
  5. stirringstirred for 5 minutes
  6. washthe organic phase was washed with water, saturated aqueous sodium bicarbonate and brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-e7772bfd0d6e48e79add95225e8c0c4c
Source dataset
uspto-grants-2014_05
Patent number
US08716493B2

Reaction notes

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