Tributylphosphine → HCID 69311489, compound

HRID 860507Notes

Reaction equation

HRID 860507 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9]3[N:10]([C:24]([CH2:27][CH3:28])=[CH:25][CH:26]=3)[N:11]=[C:12]([CH2:22]O)[C:13]=2[CH2:14][CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:5]=[N:6][CH:7]=1.C(P(CCCC)CCCC)CCC.[O:42]1[CH2:46][CH2:45][NH:44][C:43]1=[O:47].N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1(C)C=CC=CC=1.CCCCCC>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9]3[N:10]([C:24]([CH2:27][CH3:28])=[CH:25][CH:26]=3)[N:11]=[C:12]([CH2:22][N:44]3[CH2:45][CH2:46][O:42][C:43]3=[O:47])[C:13]=2[CH2:14][CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:5]=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 739492-OxazolidinoneHCID 68805475HCID 68805475, compound

Product 1

HCID 69311489HCID 69311489, compoundYield 30.9%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8058HexaneSolvent

Procedure

To a solution of ethyl 4-[4-(5-bromo-3-pyridinyl)-7-ethyl-2-(hydroxymethyl)pyrrolo[1,2-b]pyridazin-3-yl]butanoate (70.0 mg) in toluene (1 mL) was added tributylphosphine (0.098 mL), 1,3-oxazolidin-2-one (34.1 mg) in that order in an ice bath. After stirring for 5 minutes, to the mixture was added 1,1′-(azodicarbonyl)dipiperidine (98.9 mg). The mixture was stirred for 10 minutes in the bath, and 8 hours at room temperature. Hexane (5 mL) was added, and the mixture was filtered. The filtrate was evaporated. Preparative thin layer chromatography (ethyl acetate-hexane=1-1) afforded ethyl 4-{4-(5-bromo-3-pyridinyl)-7-ethyl-2-[(2-oxo-1,3-oxazolidin-3-yl)methyl]pyrrolo[1,2-b]pyridazin-3-yl}butanoate as an yellow gum (25.0 mg).

Workup

  1. stirringThe mixture was stirred for 10 minutes in the bath, and 8 hours at room temperature
  2. filtrationthe mixture was filtered
  3. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-8cee233e0044474aa3dd6ae6d2f3cc27
Source dataset
uspto-grants-2006_12
Patent number
US07153854B2

Reaction notes

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