1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 86705049, compound

HRID 1427259Notes

Reaction equation

HRID 1427259 reaction equation
[CH3:1][S:2]([CH2:5]P(=O)(OCC)OCC)(=[O:4])=[O:3].[Li+].[Cl-].C1CCN2C(=NCCC2)CC1.[Cl:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]([N:41]2[C:49]3[C:44](=[C:45]([CH:50]=O)[CH:46]=[CH:47][CH:48]=3)[CH:43]=[CH:42]2)([CH2:39][CH3:40])[C:35]([O:37][CH3:38])=[O:36])=[CH:30][CH:29]=1>CC#N.C(Cl)Cl>[Cl:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]([N:41]2[C:49]3[C:44](=[C:45](/[CH:50]=[CH:5]/[S:2]([CH3:1])(=[O:3])=[O:4])[CH:46]=[CH:47][CH:48]=3)[CH:43]=[CH:42]2)([CH2:39][CH3:40])[C:35]([O:37][CH3:38])=[O:36])=[CH:30][CH:29]=1

Participants

7

Reactant 4

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 433294Lithium ChlorideHCID 533797Diethyl (methanesulfonylmethyl)phosphonateHCID 86705048HCID 86705048, compound

Product 1

HCID 86705049HCID 86705049, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a solution of diethyl methylsulfonylmethylphosphonate (1.05 g, 4.56 mmol) in CH3CN (30 mL) at RT was added LiCl (0.16 g, 3.80 mmol) and DBU (2.40 g, 9.56 mmol). After 5 min, a solution of methyl 2-(4-chlorophenyl)-2-(4-formyl-1H-indol-1-yl)butanoate (1.35 g, 3.80 mmol) in CH3CN (10 mL) was added dropwise. The resulting mixture was stirred for 4 hours at RT. Then it was diluted with DCM (50 mL) and the organic layer was washed with water (30 mL), dried over Na2SO4, filtered. After removal of the solvent, the residue was purified via column chromatography (0-30% EtOAc/hexanes) to provide the title compound. LC/MS m/z=432.0[M+H]+.

Workup

  1. washthe organic layer was washed with water (30 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customAfter removal of the solvent
  5. customthe residue was purified via column chromatography (0-30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-f6fcc6df39154dfcadaca6fd844ee9f9
Source dataset
uspto-grants-2015_01
Patent number
US08933113B2

Reaction notes

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