Dimethylformamide → HCID 18800617, compound

HRID 1419613Notes

Reaction equation

HRID 1419613 reaction equation
CN([CH:4]=[O:5])C.O=P(Cl)(Cl)Cl.[CH2:11]([CH:18]1[CH2:23][CH2:22][N:21]([C:24]([CH2:26][N:27]2[C:35]3[C:30](=[CH:31][C:32]([C:36]#[N:37])=[CH:33][CH:34]=3)[CH:29]=[CH:28]2)=[O:25])[CH2:20][CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[CH2:38]1C[O:41][CH2:40][CH2:39]1>>[CH2:11]([CH:18]1[CH2:23][CH2:22][N:21]([C:24]([CH2:26][N:27]2[C:35]3[C:30](=[CH:31][C:32]([C:36]#[N:37])=[CH:33][CH:34]=3)[C:29]([CH2:38][CH2:39][C:40]([O:5][CH3:4])=[O:41])=[CH:28]2)=[O:25])[CH2:20][CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 8028TetrahydrofuranHCID 24813Phosphorus oxychlorideHCID 18800581HCID 18800581, compound

Product 1

HCID 18800617HCID 18800617, compound

Procedure

To a stirred solution of DMF (15 mL) and POCl3 (256 mg, 1.7 mmol) at 0° C. was added 1-(4-benzylpiperidine-carbonyl)methyl-5-cyanoindole (199 mg, 0.56 mmol). After stirring 3 h, the reaction was quenched with 2N sodium hydroxide and stirred for 30 min. It was then extracted with chloroform, dried with sodium sulfate, filtered and concentrated in vacuo to afford product. LRMS (M+H)+ 386. The product was then refluxed in the presence of triphenyl phosphonium(methylenecarbomethoxy)ylide in THF under a nitrogen atmosphere for 18 h. The reaction was concentrated in vacuo and the residue purified via silica gel chromatography using 7% MeOH/CHCl3 as the eluant to afford 140 mg of product.

Workup

  1. customthe reaction was quenched with 2N sodium hydroxide
  2. stirringstirred for 30 min
  3. extractionIt was then extracted with chloroform
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto afford product
  8. concentrationThe reaction was concentrated in vacuo
  9. customthe residue purified via silica gel chromatography

Sources & evidence

ORD record
ord-ca18efcb2632430bb8eebbb2dd28c6ff
Source dataset
uspto-grants-1999_03
Patent number
US05886191

Reaction notes

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