Lithium hydroxide, monohydrate → HCID 178515298, compound

HRID 389530Notes

Reaction equation

HRID 389530 reaction equation
FC(F)(F)S([O:6][C:7]1[CH:8]=[C:9]2[C:15]([Br:16])=[CH:14][S:13][C:10]2=[CH:11][N:12]=1)(=O)=O.O.[OH-].[Li+]>CS(C)=O>[Br:16][C:15]1[C:9]2[C:10](=[CH:11][N:12]=[C:7]([OH:6])[CH:8]=2)[S:13][CH:14]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 86662416HCID 86662416, compound

Product 1

HCID 178515298HCID 178515298, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 3-bromothieno[2,3-c]pyridin-5-yl trifluoromethanesulfonate (145 mg, 0.400 mmol), lithium hydroxide monohydrate (173 mg, 4.00 mmol) and dimethyl sulfoxide (10 mL) was heated at 75° C. for 2.5 h. The solvent was removed and the residue was neutralized with aqueous 2 N HCl. The residue was then extracted with 30% n-BuOH:EtOAc (3×50 mL). The combined organic extracts were washed with water (2×10 mL) and brine (10 mL), dried over MgSO4, and concentrated in vacuo to afford 92 mg (100%) of the title compound as a yellow solid. MS (ESI): 230.01, 231.97 [M+H]+; HPLC tR=2.46 min (ZQ3: polar—5 min).

Workup

  1. customThe solvent was removed
  2. extractionThe residue was then extracted with 30% n-BuOH
  3. washThe combined organic extracts were washed with water (2×10 mL) and brine (10 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-02ba632ffe5749fdacf2babf8192facd
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

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