Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → HCID 86602408, compound

HRID 2373223Notes

Reaction equation

HRID 2373223 reaction equation
[CH2:1]([N:3]1[C:7]2=[N:8][C:9]([CH2:23][O:24][CH3:25])=[C:10](/[CH:19]=[CH:20]/[CH2:21]O)[C:11]([C:12]3[CH:13]=[N:14][CH:15]=[C:16]([CH3:18])[CH:17]=3)=[C:6]2[CH:5]=[N:4]1)[CH3:2].C1(P(=[CH:45][C:46]([O:48][CH2:49][CH3:50])=[O:47])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[O-2].[O-2].[Mn+4].C(Cl)Cl>[CH2:1]([N:3]1[C:7]2=[N:8][C:9]([CH2:23][O:24][CH3:25])=[C:10](/[CH:19]=[CH:20]/[CH:21]=[CH:45]/[C:46]([O:48][CH2:49][CH3:50])=[O:47])[C:11]([C:12]3[CH:13]=[N:14][CH:15]=[C:16]([CH3:18])[CH:17]=3)=[C:6]2[CH:5]=[N:4]1)[CH3:2]

Participants

5

Reactant 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 11702825HCID 11702825, compound

Product 1

HCID 86602408HCID 86602408, compoundYield 110.3%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of (2E)-3-[1-ethyl-6-(methoxymethyl)-4-(5-methyl-3-pyridyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-2-propen-1-ol (40 mg), ethyl (triphenylphosphanylidene)-acetate (49 mg), manganese dioxide (103 mg) and DCM (2 ml) was stirred at room temperature for 1 h. The reaction mixture was filtrated through celite pad. The solvent was evaporated and the residue was purified by flash column chromatography on silica gel (CHCl3-MeOH 95:5) to give ethyl (2E,4E)-5-[1-ethyl-6-(methoxymethyl)-4-(5-methyl-3-pyridyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-2,4-pentadienoate (53 mg) as a colorless solid.

Workup

  1. filtrationThe reaction mixture was filtrated through celite pad
  2. customThe solvent was evaporated
  3. customthe residue was purified by flash column chromatography on silica gel (CHCl3-MeOH 95:5)

Sources & evidence

ORD record
ord-98e87021e8564977992abb5a76a7009d
Source dataset
uspto-grants-2008_12
Patent number
US07459451B2

Reaction notes

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