Potassium tert-butoxide → HCID 90313809, compound

HRID 1524161Notes

Reaction equation

HRID 1524161 reaction equation
[Br:1][C:2]1[C:3]([S:8]([CH2:11][CH2:12][CH2:13]Cl)(=[O:10])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1.CC([O-])(C)C.[K+]>C1COCC1>[Br:1][C:2]1[C:3]([S:8]([CH:11]2[CH2:13][CH2:12]2)(=[O:10])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 66127862HCID 66127862, compound

Product 1

HCID 90313809HCID 90313809, compoundYield 152.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-bromo-2-((chloropropyl)sulfonyl)pyridine (0.05 g, 89% purity, 0.2 mmol) in THF (20 mL) was added t-BuOK (0.047 g, 0.42 mmol) at −38° C. and the mixture was stirred for an additional 30 minutes. The reaction was quenched by adding saturated NH4Cl aqueous solution (2.5 mL) and concentrated to dryness. The resultant residue was diluted with water (10 mL) and extracted with DCM (2×10 mL). The combined organic extracts were dried over MgSO4, and concentrated to dryness to give the title compound (0.08 g, crude), which was used in the next step without further purification. MS (ESI): mass calcd. for C8H8BrNO2S, 260.95; m/z found, 262.0 [M+H]+.

Workup

  1. customThe reaction was quenched
  2. additionby adding saturated NH4Cl aqueous solution (2.5 mL)
  3. concentrationconcentrated to dryness
  4. additionThe resultant residue was diluted with water (10 mL)
  5. extractionextracted with DCM (2×10 mL)
  6. dry with materialThe combined organic extracts were dried over MgSO4
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-d0a5be3a202a488b960adfa7b1dc2bdc
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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