Dimethyl Sulfate → HCID 66759980, compound

HRID 389531Notes

Reaction equation

HRID 389531 reaction equation
[H-].[Na+].[Br:3][C:4]1[C:12]2[C:7](=[CH:8][N:9]=[C:10]([OH:13])[CH:11]=2)[S:6][CH:5]=1.S(OC)(O[CH3:18])(=O)=O>CN(C=O)C>[Br:3][C:4]1[C:12]2[C:7](=[CH:8][N:9]=[C:10]([O:13][CH3:18])[CH:11]=2)[S:6][CH:5]=1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 178515298HCID 178515298, compound

Product 1

HCID 66759980HCID 66759980, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Into a suspension of 60% sodium hydride (18.6 mg, 0.465 mmol) in DMF (1.0 mL) was added a solution of 3-bromothieno[2,3-c]pyridin-5-ol (54.0 mg, 0.232 mmol) in DMF (3 mL) at RT in 5 min under an atmosphere of nitrogen. After 30 min stirring at RT, dimethyl sulfate (26.9 μL, 0.279 mmol) was added. The combined mixture was stirred at RT for 16 h. After that time, the solvent was removed in vacuo. The residue was then purified by ISCO chromatography (0 to 5% MeOH:DCM) to afford 11.2 mg (20%) of the title compound as a beige solid. 1H NMR (400 MHz, DMSO-d6): δ 8.95 (d, J=0.8 Hz, 1H), 8.31 (s, 1 H), 7.01 (d, J=0.8 Hz, 1 H), 3.94 (s, 3 H); MS (ESI): 243.94, 245.90 [M+H]+; HPLC tR=4.15 min (ZQ3: polar—5 min).

Workup

  1. stirringThe combined mixture was stirred at RT for 16 h
  2. customAfter that time, the solvent was removed in vacuo
  3. customThe residue was then purified by ISCO chromatography (0 to 5% MeOH:DCM)

Sources & evidence

ORD record
ord-5df6010b0ec04f8f9c7510ebbe905815
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

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