HCID 68554748, compound → HCID 68553646, compound

HRID 1868145Notes

Reaction equation

HRID 1868145 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]1[CH2:14][CH2:13][N:12]([S:15]([C:18]2[CH:23]=[CH:22][C:21]([C:24](=[O:26])[CH3:25])=[CH:20][CH:19]=2)(=[O:17])=[O:16])[C@H:11]([CH3:27])[CH2:10]1.[Li][CH3:29]>C1COCC1>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]1[CH2:14][CH2:13][N:12]([S:15]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([OH:26])([CH3:29])[CH3:25])=[CH:20][CH:19]=2)(=[O:17])=[O:16])[C@H:11]([CH3:27])[CH2:10]1

Participants

4

Reactant 2

HCID 68554748HCID 68554748, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 68553646HCID 68553646, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (R)-1-(4-(4-(2,4-difluorophenyl)-2-methylpiperazin-1-ylsulfonyl)phenyl)ethanone (220 mg, 0.558 mmol, prepared according to procedures similar to those described in Example 29A in THF (3 mL) was added MeLi (0.42 mL, 1.6 M in THF, 0.67 mmol) at −78° C. The resultant mixture was stirred for 6 h then quenched with aq. NH4Cl and aq. layer. It was extracted with DCM. The organic layer was dried over Na2SO4. The crude product was purified on SiO2 column eluted with hexanes/EtOAc to give the desired product as a white solid (167 mg, 73%). HRMS: calcd for C20H24F2N2O3S+H+, 411.15484. found (ESI-FTMS, [M+H]1+), 411.15477.

Workup

  1. customthen quenched with aq. NH4Cl and aq. layer
  2. extractionIt was extracted with DCM
  3. dry with materialThe organic layer was dried over Na2SO4
  4. customThe crude product was purified on SiO2 column
  5. washeluted with hexanes/EtOAc

Sources & evidence

ORD record
ord-3c2aedfff6514b9698e638bc64d42ef9
Source dataset
uspto-grants-2009_12
Patent number
US07632838B2

Reaction notes

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