Perchloric Acid → Methyl 2-{3-bromothieno[2,3-b]pyridin-2-yl}-2-(tert-butoxy)acetate

HRID 591008Notes

Reaction equation

HRID 591008 reaction equation
Cl(O)(=O)(=O)=O.[Br:6][C:7]1[C:15]2[C:10](=[N:11][CH:12]=[CH:13][CH:14]=2)[S:9][C:8]=1[CH:16]([OH:21])[C:17]([O:19][CH3:20])=[O:18]>C(OC(C)(C)C)(=O)C>[Br:6][C:7]1[C:15]2[C:10](=[N:11][CH:12]=[CH:13][CH:14]=2)[S:9][C:8]=1[CH:16]([O:21][C:15]([CH3:7])([CH3:10])[CH3:14])[C:17]([O:19][CH3:20])=[O:18]

Participants

4

Reactant 2

HCID 24247Perchloric AcidHCID 70855401Methyl 2-{3-bromothieno[2,3-b]pyridin-2-yl}-2-hydroxyacetate

Product 1

HCID 70855404Methyl 2-{3-bromothieno[2,3-b]pyridin-2-yl}-2-(tert-butoxy)acetateYield 50%

Reagents, catalysts & solvents 1

HCID 10908tert-Butyl acetateSolvent

Procedure

Under a nitrogen atmosphere, perchloric acid (70%, 750 μL) was added at −10° C. to a solution of methyl 2-{3-bromothieno[2,3-b]pyridin-2-yl}-2-hydroxyacetate (14f) (180 mg, 0.6 mmol) in tertbutyl acetate (5 mL). After 1 hour, the reaction was quenched with a saturated aqueous solution of sodium bicarbonate and extracted with dichloromethane (2×10 mL). The organic layer was washed with brine (10 mL), dried over sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel (dichloromethane/ethyl acetate 90/10) to afford the desired product (14g) as a white solid (55 mg, 0.15 mmol, 26%).

Workup

  1. customthe reaction was quenched with a saturated aqueous solution of sodium bicarbonate
  2. extractionextracted with dichloromethane (2×10 mL)
  3. washThe organic layer was washed with brine (10 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe residue was purified by flash chromatography on silica gel (dichloromethane/ethyl acetate 90/10)

Sources & evidence

ORD record
ord-8dc5ce3cb0ea43b798e1e79d5f9db786
Source dataset
uspto-grants-2016_01
Patent number
US09238026B2

Reaction notes

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