Triethylamine → (S)-8-bromo-2,3-dihydro-[1,4]dioxino[2,3-b]pyridine-3-methanol methanesulfonate

HRID 1793328Notes

Reaction equation

HRID 1793328 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[O:8][CH:9]([CH2:12][OH:13])[CH2:10][O:11][C:3]=12.C(N(CC)CC)C.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>C(Cl)Cl>[CH3:21][S:22]([O:13][CH2:12][C@H:9]1[O:8][C:4]2=[N:5][CH:6]=[CH:7][C:2]([Br:1])=[C:3]2[O:11][CH2:10]1)(=[O:24])=[O:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 22020941HCID 22020941, compound

Product 1

HCID 131725871(S)-8-bromo-2,3-dihydro-[1,4]dioxino[2,3-b]pyridine-3-methanol methanesulfonateYield 92.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of intermediate (42) (0.0014 mol) and triethylamine (0.0028 mol) in DCM (5 ml), methanesulfonyl chloride (0.0021 mol) was slowly added at room temperature. The reaction mixture was stirred for 16 hours and was then extracted with water. The separated organic layer was dried, filtered and the solvent was evaporated, yielding 0.42 g of (S)-8-bromo-2,3-dihydro-[1,4]dioxino[2,3-b]pyridine-3-methanol methanesulfonate (ester) (intermediate (43).

Workup

  1. additionwas slowly added at room temperature
  2. extractionwas then extracted with water
  3. customThe separated organic layer was dried
  4. filtrationfiltered
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-7a5b96a352424d638904a6a376f3d613
Source dataset
uspto-grants-2006_07
Patent number
US07081453B2

Reaction notes

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