Benzenesulfonyl chloride → 1-(Benzenesulfonyl)-3-iodo-5-(phenylsulfanyl)-1H-pyrrolo[2,3-b]pyridine

HRID 1991095Notes

Reaction equation

HRID 1991095 reaction equation
[I:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([S:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:9]=2)[NH:4][CH:3]=1.[C:18]1([S:24](Cl)(=[O:26])=[O:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[OH-].[Na+]>C(Cl)Cl>[C:18]1([S:24]([N:4]2[C:5]3=[N:6][CH:7]=[C:8]([S:11][C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=4)[CH:9]=[C:10]3[C:2]([I:1])=[CH:3]2)(=[O:26])=[O:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 591287053-Iodo-5-(phenylsulfanyl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 591286551-(Benzenesulfonyl)-3-iodo-5-(phenylsulfanyl)-1H-pyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3 (200 mg, 0.57 mmol), benzenesulfonyl chloride (109 μL, 0.85 mmol), n-BuNHSO4 (25 mg, 0.074 mmol) and 50% aqueous NaOH (108 μL) in CH2Cl2 (3.5 mL) were stirred for 0.5 h. The mixture was partitioned between sat. aq. NaHCO3/CH2Cl2. The organic layer was separated and the aqueous phase extracted with CH2Cl2. The combined organic solutions were dried (MgSO4) and concentrated to give 4 as an orange oil (336 mg, 120

Workup

  1. customThe mixture was partitioned between sat. aq. NaHCO3/CH2Cl2
  2. customThe organic layer was separated
  3. extractionthe aqueous phase extracted with CH2Cl2
  4. dry with materialThe combined organic solutions were dried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7cc1658bad3b4c1f972887494d82929c
Source dataset
uspto-grants-2010_01
Patent number
US07645769B2

Reaction notes

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