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

HRID 1661657Notes

Reaction equation

HRID 1661657 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-89288ef5fe464c589cdeef7a6e39d7f6
Source dataset
uspto-grants-2011_10
Patent number
US08030334B2

Reaction notes

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