Water → 5-Bromo-1-(methanesulfonyl)-1H-pyrrolo[2,3-b]pyridine

HRID 269489Notes

Reaction equation

HRID 269489 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[H-].[Na+].[CH3:13][S:14](Cl)(=[O:16])=[O:15].O>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][N:8]([S:14]([CH3:13])(=[O:16])=[O:15])[C:5]2=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 31297Methanesulfonyl chlorideHCID 103079325-bromo-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 497588975-Bromo-1-(methanesulfonyl)-1H-pyrrolo[2,3-b]pyridineYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-bromo-1H-pyrrolo[2,3-b]pyridine (600 mg, 3.06 mmol) in dry THF (30 mL) was added NaH (246 mg, 6.12 mmol) at room temperature. The suspension was stirred for 30 min before addition of methanesulfonyl chloride (540 mg, 4.80 mmol). The solution was stirred at room temperature for another 30 min and poured into water (50 mL). The aqueous solution was extracted with ethyl acetate (2×30 mL), the combined organic layers were dried over MgSO4 and filtered, the filtrate was evaporated under vacuum to afford white solid (780 mg, 93%). The crude product was used directly for the next reaction. LC/MS: Rt 3.26 mis.; (m/e=275.0, 276.9 (M+H, M+2+H).

Workup

  1. extractionThe aqueous solution was extracted with ethyl acetate (2×30 mL)
  2. dry with materialthe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. customthe filtrate was evaporated under vacuum

Sources & evidence

ORD record
ord-b52bd419eb1f4f729888f8c98810de78
Source dataset
uspto-grants-2008_11
Patent number
US07446199B2

Reaction notes

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