Triphenylphosphine → HCID 22933553, compound

HRID 1269798Notes

Reaction equation

HRID 1269798 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([OH:10])=[CH:7][CH:8]=2)[CH:3]=[N:2]1.O[CH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.C1(C)C=CC=CC=1>O1CCCC1>[O:15]1[CH2:16][CH2:17][CH:12]([O:10][C:6]2[CH:5]=[C:4]3[C:9](=[CH:8][CH:7]=2)[NH:1][N:2]=[CH:3]3)[CH2:13][CH2:14]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 74956Tetrahydro-4H-pyran-4-olHCID 1014381H-Indazol-5-olHCID 66777355Diethylazodicarboxylate toluene

Product 1

HCID 22933553HCID 22933553, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the 1H-indazol-5-ol (150 mg, 1.12 mmol) obtained in Reference Example 4 in tetrahydrofuran (6 ml) were added 4-hydroxytetrahydropyran (0.107 ml, 1.12 mmol), triphenylphosphine (293 mg, 1.12 mmol) and a 40%-diethyl azodicarboxylate-toluene solution (0.517 ml, 1.14 mmol) at 0° C. After 30 minutes, the mixture thus obtained was heated 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/methanol) to obtain 5-(tetrahydro-2H-pyran-4-yloxy)-1H-indazole (11.4 mg, 47%).

Workup

  1. customat 0° C
  2. customthe mixture thus obtained
  3. concentrationthe reaction solution was concentrated under reduced pressure
  4. customthe resulting residue was purified by a silica gel column chromatography (eluent: chloroform/methanol)

Sources & evidence

ORD record
ord-868589481e18464d8025e7f0bdb69e94
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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