HCID 21099386, compound → HCID 21099380, compound

HRID 2376993Notes

Reaction equation

HRID 2376993 reaction equation
F[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1/[CH:9]=[CH:10]/[C:11]1[CH:16]=[CH:15][C:14]([S:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[C:26](=[O:28])[CH3:27])(=[O:19])=[O:18])=[CH:13][CH:12]=1.[CH3:29][Mg]Br>C1COCC1>[F:8][C:6]1[CH:5]=[CH:4][C:3](/[CH:9]=[CH:10]/[C:11]2[CH:16]=[CH:15][C:14]([S:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:26]([OH:28])([CH3:29])[CH3:27])(=[O:18])=[O:19])=[CH:13][CH:12]=2)=[CH:2][CH:7]=1

Participants

4

Reactant 2

HCID 21099386HCID 21099386, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 21099380HCID 21099380, compoundYield 78.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred THF (1 mL) solution of 1-[2-({4-[(E)-2-(2,4-difluorophenyl)vinyl]phenyl}sulfonyl)phenyl]ethanone (Example 141; 65 mg, 0.17 mmol) was treated with methyl magnesium bromide (3 N in Et2O; 0.17 mL, 0.51 mmol) at ambient temperature. After 75 minutes, the mixture was partitioned between water (20 mL) and EtOAc (20 mL). The phases were separated and the organic phase dried (MgSO4), filtered and concentrated in vacuo. The crude material was purified by flash chromatography on silica (eluant 35% EtOAc/isohexane). The material thus obtained was washed with hexane to afford the title compound as a white solid (53 mg). δH (500 MHz, d6 DMSO): 8.25 (1H, d, J 8.1), 7.71-7.64 (8H, m), 7.53 (1H, t, J 6.1), 7.40 (1H, d, J 16.4), 7.30-7.22 (3H, m), 4.98 (1H, s), 1.56 (6H, s). m/z (ES+) 419 [(M+Na)+].

Workup

  1. customthe mixture was partitioned between water (20 mL) and EtOAc (20 mL)
  2. customThe phases were separated
  3. dry with materialthe organic phase dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified by flash chromatography on silica (eluant 35% EtOAc/isohexane)
  7. customThe material thus obtained
  8. washwas washed with hexane

Sources & evidence

ORD record
ord-c152abe13eaa4bf8ad1cd32d39cec338
Source dataset
uspto-grants-2008_12
Patent number
US07468393B2

Reaction notes

Loading…