Sodium Methoxide → HCID 21099395, compound

HRID 1351698Notes

Reaction equation

HRID 1351698 reaction equation
F[C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[CH:4][C:3]=1[S:10]([C:13]1[CH:18]=[CH:17][C:16](/[CH:19]=[CH:20]/[C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)=[CH:15][CH:14]=1)(=[O:12])=[O:11].[CH3:28][O-:29].[Na+]>>[F:27][C:24]1[CH:23]=[CH:22][C:21](/[CH:20]=[CH:19]/[C:16]2[CH:17]=[CH:18][C:13]([S:10]([C:3]3[CH:4]=[CH:5][CH:6]=[C:7]([O:8][CH3:9])[C:2]=3[O:29][CH3:28])(=[O:11])=[O:12])=[CH:14][CH:15]=2)=[CH:26][CH:25]=1

Participants

3

Reactant 2

HCID 10942334Sodium Methoxide2×HCID 21099475HCID 21099475, compound

Product 1

HCID 21099395HCID 21099395, compound

Conditions

Temperature
150 °C

Procedure

A mixture of 2-fluoro-1-({4-[(E)-2-(4-fluorophenyl)vinyl]phenyl}sulfonyl)-3-methoxybenzene (Example 192, 45 mg, 0.116 mmol) and sodium methoxide (0.5M in methanol, 1 mL) was heated to 150° C. for 10 minutes in a microwave reactor. A further 0.5 mL sodium methoxide was added and heating continued at 150° C. for 30 minutes. The cooled reaction mixture was partitioned between water and ethyl acetate. The organic layer was washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica, eluting with 20% ethyl acetate/isohexane, to give the title compound. δH (500 MHz, d6 DMSO): 7.91 (2H, d, J=8.5 Hz), 7.76 (2H, d, J=8.4 Hz), 7.67 (2H, dd, J=5.7, 8.7 Hz), 7.52 (1H, dd, J=2.2, 8.5 Hz), 7.39 (2H, d, J=2.3 Hz), 7.28 (1H, s), 7.25–7.19 (2H, m), 7.14 (1H, d, J=8.6 Hz), 3.82 (3H, s), 3.80 (3H, s).

Workup

  1. temperatureheating
  2. customThe cooled reaction mixture
  3. customwas partitioned between water and ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash column chromatography on silica
  8. washeluting with 20% ethyl acetate/isohexane

Sources & evidence

ORD record
ord-082b49edff5042af811303083c140a52
Source dataset
uspto-grants-2007_05
Patent number
US07217740B2

Reaction notes

Loading…