Triphenylphosphine → HCID 11640032, compound

HRID 2108758Notes

Reaction equation

HRID 2108758 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][C:10]([NH:12][C:13]2[S:14][CH:15]=[C:16]([C:18]3[C:26]4[C:21](=[N:22][CH:23]=[CH:24][CH:25]=4)[NH:20][CH:19]=3)[N:17]=2)=[O:11])[CH:6]=[CH:7][CH:8]=1.[CH:27]1[CH:32]=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=C[CH:28]=1.BrCCCO.CC(OC(/N=N/C(OC(C)C)=O)=O)C.[H-].[Na+]>C1COCC1.CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]2[CH2:32][CH2:27][CH2:28][N:12]([C:13]3[S:14][CH:15]=[C:16]([C:18]4[C:26]5[C:21](=[N:22][CH:23]=[CH:24][CH:25]=5)[NH:20][CH:19]=4)[N:17]=3)[C:10]2=[O:11])[CH:6]=[CH:7][CH:8]=1

Participants

8

Reactant 5

HCID 11776TriphenylphosphineHCID 123083-Bromo-1-propanolHCID 24758Sodium hydrideHCID 5363146Diisopropyl azodicarboxylateHCID 11581362HCID 11581362, compound

Product 1

HCID 11640032HCID 11640032, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 2-(3-methoxy-phenyl)-N-[4-(1H-pyrrolo[2,3-b]pyridin-3-yl)-thiazol-2-yl]-acetamide (1 mmol) in THF was added 1.2 mmol of PPh3, 1.2 mmol of 3-bromopropanol and 1.2 mmol of DIAD and the reaction mixture was stirred at room temperature for 16 h. The reaction mixture was cooled to 0° C. and 1.2 mmol of NaH was added and reaction mixture was stirred at 0° C. for 30 minutes. MeOH was added to quench reaction and the solvent evaporated. The residue was redissolved in EtOAc and the organic layer was washed with H2O and dried over Na2SO4. After removal of solvent, the final product was purified by preparative HPLC to afford 3-(3-methoxy-phenyl)-1-[4-(1H-pyrrolo[2,3-b]pyridin-3-yl)-thiazol-2-yl]-piperidin-2-one in 30% yield.

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. customreaction mixture
  3. stirringwas stirred at 0° C. for 30 minutes
  4. customto quench
  5. customreaction
  6. customthe solvent evaporated
  7. dissolutionThe residue was redissolved in EtOAc
  8. washthe organic layer was washed with H2O
  9. dry with materialdried over Na2SO4
  10. customAfter removal of solvent
  11. customthe final product was purified by preparative HPLC

Sources & evidence

ORD record
ord-c62e53eb2bc94acd9babbed385560fc0
Source dataset
uspto-grants-2009_04
Patent number
US07514448B2

Reaction notes

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