Sodium Methoxide → HCID 50994578, compound

HRID 1784856Notes

Reaction equation

HRID 1784856 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:17][S:18]([CH3:21])(=[O:20])=[O:19])[CH:5]=[C:6]([C:8]([C:10]2[CH:15]=[CH:14][N:13]=[C:12](Cl)[CH:11]=2)=[O:9])[CH:7]=1.[CH3:22][O-:23].[Na+]>CO>[Br:1][C:2]1[CH:3]=[C:4]([NH:17][S:18]([CH3:21])(=[O:20])=[O:19])[CH:5]=[C:6]([C:8]([C:10]2[CH:15]=[CH:14][N:13]=[C:12]([O:23][CH3:22])[CH:11]=2)=[O:9])[CH:7]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 50994437HCID 50994437, compound

Product 1

HCID 50994578HCID 50994578, compoundYield 43.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 0.080 g (0.21 mmol) of N-[3-bromo-5-(2-chloro-pyridine-4-carbonyl)-phenyl]-methanesulfonamide in 10.0 mL of anhydrous methanol in a pressure tube was added 0.007 g (0.21 mmol) of sodium methoxide. The tube was sealed and the reaction was heated at 80° C. for 18 hours. The methanol was removed under vacuum and water was added to the reaction mixture. The aqueous phase was extracted with ethyl acetate, washed with water and brine and dried over anhydrous sodium sulfate. The solution was filtered and concentrated to give 0.035 g of N-[3-bromo-5-(2-methoxy-pyridine-4-carbonyl)-phenyl]-methanesulfonamide. The Suzuki reaction and removal of the triisopropylsilyl protecting group were carried out as described in Example 35. 1H NMR (400 MHz, CD3COCD3): δ 10.49 (s, 1H), 8.96 (s, 1H), 8.38 (d, J=5.1 Hz, 1H), 8.07 (t, J=1.9 Hz, 1H), 7.90 (t, J=1.6 Hz, 1H), 7.83 (t, J=1.9 Hz, 1H), 7.51 (d, J=7.8 Hz, 1H), 7.45 (t, J=2.8 Hz, 1H), 7.30 (dd, J=5.1, 1.3 Hz, 1H), 7.26-7.18 (m, 2H), 7.10 (s, 1H), 6.75-6.72 (m, 1H), 3.96 (s, 3H), 3.15 (s, 3H).

Workup

  1. customThe tube was sealed
  2. customThe methanol was removed under vacuum and water
  3. additionwas added to the reaction mixture
  4. extractionThe aqueous phase was extracted with ethyl acetate
  5. washwashed with water and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationThe solution was filtered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-0e72776a19224d0aaa321979d502a209
Source dataset
uspto-grants-2009_03
Patent number
US07504401B2

Reaction notes

Loading…