Benzenesulfonyl chloride → 1-(Benzenesulfonyl)-3-iodo-1H-pyrrolo[2,3-b]pyridine

HRID 1787577Notes

Reaction equation

HRID 1787577 reaction equation
[I:1]Cl.[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][N:10]=2)[CH:5]=[CH:4]1.C(N(CC)CC)C.[C:19]1([S:25](Cl)(=[O:27])=[O:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(Cl)Cl.N1C=CC=CC=1.C(OCC)(=O)C.CN(C1C=CN=CC=1)C>[C:19]1([S:25]([N:3]2[C:11]3=[N:10][CH:9]=[CH:8][CH:7]=[C:6]3[C:5]([I:1])=[CH:4]2)(=[O:27])=[O:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

9

Reactant 4

HCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 92221H-Pyrrolo(2,3-b)pyridineHCID 24640Iodine chloride

Product 1

HCID 242292281-(Benzenesulfonyl)-3-iodo-1H-pyrrolo[2,3-b]pyridineYield 64%

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent2×

Procedure

Add a solution of iodine monochloride (0.76 g, 4.7 mmol) in methylene chloride (4 mL) into a solution of 7-azaindole (Aldrich; 0.5 g, 4.2 mmol) in pyridine (4 mL) at 0° C. Stir the reaction at 0° C. for 15 min, then at room temperature for 30 min. Dilute with ethyl acetate and wash the organic phase with 1N aqueous hydrochloric acid (50 mL) and 1N aqueous sodium hydroxide (50 mL). Dry the organic layer (magnesium sulfate), filter, and concentrate in vacuo. Add DMAP (52 mg, 0.42 mmol), methylene chloride (14 mL), triethylamine (1.2 mL, 8.5 mmol), and benzenesulfonyl chloride (0.8 mL, 6.4 mmol) to the residue. Stir the mixture at room temperature for 18 h, then dilute with ethyl acetate. Wash the organic layer with 1N aqueous hydrochloric acid and saturated aqueous sodium bicarbonate. Dry the organic layer (sodium sulfate), filter, concentrate in vacuo, and purify by chromatography (silica gel, appropriate mixture of ethyl acetate and hexanes) to provide 1.0 g (64%) of the title compound as a tan solid. MS (ES) m/z=385 (M+H).

Workup

  1. customthe reaction at 0° C. for 15 min
  2. washwash the organic phase with 1N aqueous hydrochloric acid (50 mL) and 1N aqueous sodium hydroxide (50 mL)
  3. dry with materialDry the organic layer (magnesium sulfate)
  4. filtrationfilter
  5. concentrationconcentrate in vacuo
  6. stirringStir the mixture at room temperature for 18 h
  7. washWash the organic layer with 1N aqueous hydrochloric acid and saturated aqueous sodium bicarbonate
  8. dry with materialDry the organic layer (sodium sulfate)
  9. filtrationfilter
  10. concentrationconcentrate in vacuo
  11. custompurify by chromatography (silica gel, appropriate mixture of ethyl acetate and hexanes)

Sources & evidence

ORD record
ord-c3650d1852364983bc95078ec95f688b
Source dataset
uspto-grants-2009_03
Patent number
US07511056B2

Reaction notes

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