Triphenylphosphine → HCID 22934049, compound

HRID 1269800Notes

Reaction equation

HRID 1269800 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][CH:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:3]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC1C=CC=CC=1)=O)=NC(OCC1C=CC=CC=1)=O.[NH:54]1[C:62]2[C:57](=[CH:58][C:59](O)=[CH:60][CH:61]=2)[CH:56]=[N:55]1>O1CCCC1>[NH:54]1[C:62]2[C:57](=[CH:58][C:59]([O:1][CH:2]3[CH2:3][CH2:4][CH:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:6][CH2:7]3)=[CH:60][CH:61]=2)[CH:56]=[N:55]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 755571,2-Bis(phenylmethyl) 1,2-diazenedicarboxylateHCID 86973Ethyl 4-hydroxycyclohexanecarboxylateHCID 1014381H-Indazol-5-ol

Product 1

HCID 22934049HCID 22934049, compoundYield 43.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 4-hydroxycyclohexylcarboxylate (1.44 ml, 8.95 mmol), triphenylphosphine (2.15 g, 8.20 mmol) and dibenzyl azodicarboxylate (3.34 g, 11.18 mmol) were added at 0° C. to a solution of the 1H-indazol-5-ol (1.0 g, 7.45 mmol) obtained in Reference Example 4 in tetrahydrofuran (40 ml). After 1 hour, the mixture thus obtained was warmed up to room temperature. After stirring overnight, the reaction solution was concentrated under reduced pressure, and the resulting residue was purified by a silica gel column chromatography (eluent: chloroform/ethyl acetate, hexane/ethyl acetate) to obtain ethyl 4-(1H-indazol-5-yloxy)cyclohexanecarboxylate (928 mg, 43%).

Workup

  1. customthe mixture thus obtained
  2. concentrationthe reaction solution was concentrated under reduced pressure
  3. customthe resulting residue was purified by a silica gel column chromatography (eluent: chloroform/ethyl acetate, hexane/ethyl acetate)

Sources & evidence

ORD record
ord-ad153aaf12c14285b446bdeb05e2e694
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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