Potassium Phosphate, Tribasic → Morpholine-4-sulfonic acid 5-bromo-pyridin-3-yl ester

HRID 593612Notes

Reaction equation

HRID 593612 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[N:6][CH:7]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[N:17]1([S:23](Cl)(=[O:25])=[O:24])[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1.C([O-])(O)=O.[Na+]>O.CC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([O:8][S:23]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)(=[O:25])=[O:24])[CH:5]=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 516892Sodium BicarbonateHCID 5995293-Bromo-5-hydroxypyridineHCID 12798265Morpholine-4-sulfonyl chloride

Product 1

HCID 58215797Morpholine-4-sulfonic acid 5-bromo-pyridin-3-yl ester

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A flask is charged with 5-bromo-pyridin-3-ol (0.310 g, 1.78 mmol), potassium phosphate (0.982 g, 4.63 mmol) and acetone (10 mL), and morpholine-4-sulfonyl chloride (0.529 g, 2.85 mmol) is added dropwise at 0° C. The mixture is stirred at room temperature overnight. Saturated NaHCO3 in water (1 mL) is added and the mixture is concentrated in vacuo. The residue is purified on silica gel chromatography eluting with a 9:1 to 4:1 heptane-ethyl acetate gradient to give morpholine-4-sulfonic acid 5-bromo-pyridin-3-yl ester. MS (ESI) m/z 322.9 and 324.9 (M+H)+.

Workup

  1. additionis added dropwise at 0° C
  2. concentrationthe mixture is concentrated in vacuo
  3. customThe residue is purified on silica gel chromatography
  4. washeluting with a 9:1 to 4:1 heptane-ethyl acetate gradient

Sources & evidence

ORD record
ord-a673f2866b9946bda0915c0d67c5fdf9
Source dataset
uspto-grants-2016_01
Patent number
US09242963B2

Reaction notes

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