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

HRID 522227

Reaction equation

HRID 522227 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([S:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)(=[O:13])=[O:12])[CH:9]=[CH:10][C:3]=12.C([N-]C(C)C)(C)C.[Li+].[I:28]I>O1CCCC1>[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([S:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)(=[O:13])=[O:12])[C:9]([I:28])=[CH:10][C:3]=12

Participants

5

Reactant 3

HCID 807IodineHCID 2724682Lithium diisopropylamideHCID 450745614-Bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-B]pyridine

Product 1

HCID 469079554-Bromo-2-iodo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a −78° C. solution of Example 135A (250 mg, 0.741 mmol) in 10 mL tetrahydrofuran was added lithium diisopropylamide (2.0M solution in tetrahydrofuran, 0.556 mL, 1.112 mmol) slowly over the course of 5 minutes. The resulting solution was stirred at the same temperature for 30 minutes after which iodine (376 mg, 1.483 mmol) in 5 mL of tetrahydrofuran was slowly added over 10 minutes. The reaction was stirred at −78° C. for 2.5 hours, and was quenched by addition of 1M aqueous sodium thiosulfate solution. The mixture was extracted with dichloromethane. The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated to give the title compound. MS (ESI+) m/z 462 (M+1).

Workup

  1. additionwas slowly added over 10 minutes
  2. customwas quenched by addition of 1M aqueous sodium thiosulfate solution
  3. extractionThe mixture was extracted with dichloromethane
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-18091cced3024011912f07ec0df5ca20
Source dataset
uspto-grants-2016_05
Patent number
US09328112B2

Linked notes

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