Benzenesulfonyl chloride → 1-Benzenesulfonyl-3-iodo-5-morpholin-4-yl-1H-pyrrolo[2,3-b]pyridine

HRID 2114070Notes

Reaction equation

HRID 2114070 reaction equation
[C:1]1([S:7](Cl)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].[I:13][C:14]1[C:22]2[C:17](=[N:18][CH:19]=[C:20]([N:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)[CH:21]=2)[NH:16][CH:15]=1.C([O-])(O)=O.[Na+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl.CO>[C:1]1([S:7]([N:16]2[C:17]3=[N:18][CH:19]=[C:20]([N:23]4[CH2:24][CH2:25][O:26][CH2:27][CH2:28]4)[CH:21]=[C:22]3[C:14]([I:13])=[CH:15]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 4

HCID 7369Benzenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 598119141H-Pyrrolo[2,3-b]pyridine, 3-iodo-5-(4-morpholinyl)-

Product 1

HCID 670515121-Benzenesulfonyl-3-iodo-5-morpholin-4-yl-1H-pyrrolo[2,3-b]pyridineYield 64.7%

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Tetrabutylammonium hydrogen sulfate (0.020 g, 0.059 mmol), benzenesulfonyl chloride (0.055 mL, 0.43 mmol) and 50% aqueous NaOH solution (0.20 mL) were added to a solution of 54 (0.095 g, 0.29 mmol) in CH2Cl2 (3 mL). After stirring for 2 hours, the mixture was poured into saturated aqueous NaHCO3 solution and extracted with CH2Cl2 three times. The combined organic solutions were washed with saturated aqueous NaHCO3 solution, dried (MgSO4), and concentrated to afford a tan syrup. MeOH was added to the syrup and the mixture was cooled in an ice bath. The precipitate was filtered off, washed with MeOH and dried to afford 55 (0.088 g) as a brown solid. The filtrate was concentrated and purified by means of preparative TLC with hexane:AcOEt as eluent to afford additional 55 (0.016 g, total yield: 0.104 g, 77%) as a brown solid. 1H NMR (400 MHz, CDCl3) δ 3.08-3.12 (m, 4H), 3.80-3.84 (m, 4H), 7.00 (d, J=0.26 Hz, 1H), 7.38-7.44 (m, 2H), 7.48-7.54 (m, 1H), 7.72 (s, 1H), 8.08-8.11 (m, 2H), 8.12 (d, J=0.26 Hz, 1H).

Workup

  1. extractionextracted with CH2Cl2 three times
  2. washThe combined organic solutions were washed with saturated aqueous NaHCO3 solution
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customto afford a tan syrup
  6. temperaturethe mixture was cooled in an ice bath
  7. filtrationThe precipitate was filtered off
  8. washwashed with MeOH
  9. customdried

Sources & evidence

ORD record
ord-9a80073952414e679c4e5ee9c0e04429
Source dataset
uspto-grants-2008_10
Patent number
US07432375B2

Reaction notes

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