Dimethyl Sulfoxide → 2-(5-Bromo-2-fluoropyridin-3-yl)-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione

HRID 1621978Notes

Reaction equation

HRID 1621978 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([B:9]([OH:11])[OH:10])[C:5]([F:8])=[N:6][CH:7]=1.[CH3:12][N:13]([CH2:18][C:19](O)=[O:20])[CH2:14][C:15](O)=[O:16].CS(C)=O>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([B:9]2[O:11][C:19](=[O:20])[CH2:18][N:13]([CH3:12])[CH2:14][C:15](=[O:16])[O:10]2)[C:5]([F:8])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 20441N-methyliminodiacetic acidHCID 27832425-Bromo-2-fluoropyridine-3-boronic Acid (contains varying amounts of Anhydride)

Product 1

HCID 666007712-(5-Bromo-2-fluoropyridin-3-yl)-6-methyl-1,3,6,2-dioxazaborocane-4,8-dioneYield 82%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

5-Bromo-2-fluoropyridin-3-ylboronic acid (14.87 g, 67.7 mmol) (Frontier Scientific) and 2,2′-(methylazanediyl)diacetic acid (10.95 g, 74.4 mmol) (Aldrich) were dissolved in toluene (242 mL) and DMSO (97 mL) and the resulting mixture was heated at reflux under a Dean Stark trap for 2 h. After water (>2.5 mL) was collected in the trap, the reaction mixture was concentrated in vacuo to remove toluene, and water was slowly added to the resulting solution until the desired product precipitated as a white solid. This solid was collected by vacuum filtration, washed with water, and dried in a vacuum oven to give the title compound (82% yield) as a fluffy white solid. m/z (ESI, +ve ion) 330.8/332.9 (M+H)+.

Workup

  1. temperatureat reflux under a Dean Stark trap for 2 h
  2. customAfter water (>2.5 mL) was collected in the trap
  3. concentrationthe reaction mixture was concentrated in vacuo
  4. customto remove toluene, and water
  5. additionwas slowly added to the resulting solution until the desired product
  6. customprecipitated as a white solid
  7. filtrationThis solid was collected by vacuum filtration
  8. washwashed with water
  9. customdried in a vacuum oven

Sources & evidence

ORD record
ord-861307abbb1c4db4b1dc263fc0de1fbd
Source dataset
uspto-grants-2014_07
Patent number
US08772480B2

Reaction notes

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