Methanol → 5-Chloro-2-methoxy[1,3]thiazolo[5,4-b]pyridine

HRID 1845900Notes

Reaction equation

HRID 1845900 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]2[S:8][C:9](SC)=[N:10][C:5]2=[CH:4][CH:3]=1.[CH3:13][O-:14].[Na+].C(Cl)Cl.CO>C(OCC)(=O)C.C(O)(=O)C>[Cl:1][C:2]1[N:7]=[C:6]2[S:8][C:9]([O:14][CH3:13])=[N:10][C:5]2=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 6344DichloromethaneHCID 10942334Sodium MethoxideHCID 137996675-Chloro-2-(methylsulfanyl)[1,3]thiazolo[5,4-b]pyridine

Product 1

HCID 772309095-Chloro-2-methoxy[1,3]thiazolo[5,4-b]pyridine

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a round bottom flask was added 5-chloro-2-(methylthio)[1,3]thiazolo[5,4-b]pyridine (1-2) (11.5 g, 53.3 mmol), sodium methoxide (10.8 g, 200 mmol), anhydrous DCM (200 mL) and anhydrous MeOH (200 mL). The reaction mixture was then permitted to stir at room temperature under an atmosphere of nitrogen for 18 hours. The reaction mixture was then acidified to pH 5 with glacial acetic acid, then suspended in ethyl acetate and washed with water, then brine, dried over sodium sulfate, filtered, and concentrated. The resulting residue was purified by silica gel chromatography (0-6% IPA/DCM) to give 5-chloro-2-methoxy[1,3]thiazolo[5,4-b]pyridine (1-3) as an off-white solid. HRMS (M+H)+: observed=198.9998, calculated=198.9994.

Workup

  1. washwashed with water
  2. dry with materialbrine, dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe resulting residue was purified by silica gel chromatography (0-6% IPA/DCM)

Sources & evidence

ORD record
ord-dab13bfe6fb547bba159dc332c39e069
Source dataset
uspto-grants-2015_02
Patent number
US08952005B2

Reaction notes

Loading…