Triphenylphosphine → HCID 19805434, compound

HRID 1681701Notes

Reaction equation

HRID 1681701 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[C:13]([N:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:20](=[O:27])[NH:19]1)([O:15][CH2:16][CH3:17])=[O:14].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:47]1[CH:52]=[CH:51][CH:50]=[C:49](/[CH:53]=[CH:54]/[CH2:55]O)[CH:48]=1.N1C=CC=C(/C=C/C(OC)=O)C=1.[H-].C([Al+]CC(C)C)C(C)C>C(Cl)(Cl)Cl.C1(C)C=CC=CC=1>[C:13]([N:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:20](=[O:27])[N:19]1[CH2:55]/[CH:54]=[CH:53]/[C:49]1[CH:48]=[N:47][CH:52]=[CH:51][CH:50]=1)([O:15][CH2:16][CH3:17])=[O:14]

Participants

9

Reactant 6

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 584113Ethyl 3-oxo-2,3-dihydro-1H-indazole-1-carboxylateHCID 53576873-Pyridineacrylic acid, methyl esterHCID 5861913(2E)-3-(3-Pyridinyl)-2-propen-1-olHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 19805434HCID 19805434, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6212ChloroformSolvent2×

Procedure

A solution of diethyl azodicarboxylate (1.6 g) in chloroform (5 ml) was added dropwise to a mixture of 1,2-dihydro-1-carboethoxy-3H-indazol-3-one (1.5 g), triphenylphosphine (2 g) and trans-3-(3-pyridyl)-allyl alcohol [0.95 g; itself prepared from methyl trans-3-(3-pyridyl)-acrylate (J. Het. Chem., 1985, 22, 65) as an oil of satisfactory purity on reduction at 0° C. with a solution of di-isobutylaluminium hydride in toluene] in chloroform (20 ml). The mixture was stirred at ambient temperature for 16 hours and then evaporated to dryness. Diethyl ether was added, the mixture was filtered and the filtrate was evaporated The residue was chromatographed using an increasing gradient of ethyl acetate in petrol as eluant to give 1,2-dihydro-1-carboethoxy-2-[trans-3-(3-pyridyl)allyl]-3H-indazol-3-one (Ex. 213) as an oil (0.84 g) in 37% yield and of satisfactory purity as judged by NMR and mass spectral analysis.

Workup

  1. customevaporated to dryness
  2. additionDiethyl ether was added
  3. filtrationthe mixture was filtered
  4. customthe filtrate was evaporated The residue
  5. customwas chromatographed

Sources & evidence

ORD record
ord-479fdca7fe184fd2a0058f7ee13ca294
Source dataset
uspto-grants-1992_12
Patent number
US05173496

Reaction notes

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