HCID 67055861, compound → HCID 67055987, compound

HRID 2036801Notes

Reaction equation

HRID 2036801 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([S:12]([NH:15]C(C)(C)C)(=[O:14])=[O:13])[C:5]2[N:6]([CH:8]=[C:9]([CH3:11])[N:10]=2)[CH:7]=1>C(O)(C(F)(F)F)=O>[Br:1][C:2]1[CH:3]=[C:4]([S:12]([NH2:15])(=[O:14])=[O:13])[C:5]2[N:6]([CH:8]=[C:9]([CH3:11])[N:10]=2)[CH:7]=1

Participants

3

Reactant 1

HCID 67055861HCID 67055861, compound

Product 1

HCID 67055987HCID 67055987, compoundYield 55.4%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

6-bromo-N-tert-butyl-2-methylimidazo[1,2-a]pyridine-8-sulfonamide (1.0 g, 2.8 mmol) was stirred in TFA (6 mL) for 16 h. The TFA was removed in vacuo and a saturated solution of NaHCO3 was added. The aqueous layer was extracted with DCM, the combined organic portions dried, filtered and concentrated to yield 6-bromo-2-methylimidazo[1,2-a]pyridine-8-sulfonamide (0.45 g, 54%), which was used without further purification. LCMS Method Y: retention time 1.44 min; [M+1]=292.16.

Workup

  1. customThe TFA was removed in vacuo
  2. additiona saturated solution of NaHCO3 was added
  3. extractionThe aqueous layer was extracted with DCM
  4. customthe combined organic portions dried
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f9a1af4a130248db9305b3b9ffda83db
Source dataset
uspto-grants-2013_11
Patent number
US08575184B2

Reaction notes

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