Triethylamine → 5-(((Methanesulfonyl)oxy)methyl)-2-methylthiazolo[5,4-b]pyridine

HRID 2259525Notes

Reaction equation

HRID 2259525 reaction equation
[OH:1][CH2:2][C:3]1[N:8]=[C:7]2[S:9][C:10]([CH3:12])=[N:11][C:6]2=[CH:5][CH:4]=1.C(N(CC)CC)C.[CH3:20][S:21](Cl)(=[O:23])=[O:22].C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:20][S:21]([O:1][CH2:2][C:3]1[N:8]=[C:7]2[S:9][C:10]([CH3:12])=[N:11][C:6]2=[CH:5][CH:4]=1)(=[O:23])=[O:22]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 190028842-methylThiazolo[5,4-b]pyridine-5-methanol

Product 1

HCID 220687645-(((Methanesulfonyl)oxy)methyl)-2-methylthiazolo[5,4-b]pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of the alcohol of Step 6 (303 mg, 1.68 mmol) in 17 mL of CH2Cl2 at -40° C., triethylamine (350 μl, 2.5 mmol) and methane-sulfonyl chloride (170 μl, 2.2 mmol) were added and the solution was stirred at -40° C. for 30 min and at 0° C. for 2 hr. Saturated aq. NaHCO3 was added and the product was extracted in CH2C12, dried over Na2SO4, concentrated, and the remaining water was stripped with toluene twice.

Workup

  1. extractionthe product was extracted in CH2C12
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-61836e9bf8f24e73a97f3cc854334b1f
Source dataset
uspto-grants-1995_12
Patent number
US05472964

Reaction notes

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