Methanol → 5-Methoxy-1H-indazole

HRID 1482915Notes

Reaction equation

HRID 1482915 reaction equation
C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CO.O[C:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[NH:25][N:24]=1.C[CH2:33][O:34]C(/N=N/C(OCC)=O)=O.N#N>C1COCC1>[CH3:33][O:34][C:29]1[CH:30]=[C:31]2[C:26](=[CH:27][CH:28]=1)[NH:25][N:24]=[CH:23]2

Participants

7

Reactant 5

HCID 887MethanolHCID 947NitrogenHCID 11776TriphenylphosphineHCID 81829IndazolinoneHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 133468605-Methoxy-1H-indazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred mixture of PPh3 (1.67 g, 6.4 mmol), MeOH (204 mg, 6.4 mmol) and the hydroxyindazole prepared above (2.0 g, 5.3 mmol) in THF (20 mL) was added DEAD (1.11 g, 6.4 mmol) dropwise under N2. The resulting mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure and the residue was purified with flash chromatography on silica gel (gradient elution with 50:1 to 5:1 petroleum ether:EtOAc) to afford the desired 5-methoxyindazole as a yellow oil. MS (ESI) m/z=391.1 [M+1]+.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified with flash chromatography on silica gel (gradient elution with 50:1 to 5:1 petroleum ether:EtOAc)

Sources & evidence

ORD record
ord-16e64f0627c4428b98f8912b7c21659d
Source dataset
uspto-grants-2016_08
Patent number
US09416126B2

Reaction notes

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