Isopropanol → methyl 4-(2-propoxy)-1H-indole-2-carboxylate

HRID 2267728Notes

Reaction equation

HRID 2267728 reaction equation
CCOC(/N=N/C(OCC)=O)=O.[CH3:13][O:14][C:15]([C:17]1[NH:18][C:19]2[C:24]([CH:25]=1)=[C:23]([OH:26])[CH:22]=[CH:21][CH:20]=2)=[O:16].[C:27]1(P(C2C=CC=CC=2)C2C=CC=CC=2)[CH:32]=CC=C[CH:28]=1.C(O)(C)C>C1COCC1>[CH3:13][O:14][C:15]([C:17]1[NH:18][C:19]2[C:24]([CH:25]=1)=[C:23]([O:26][CH:27]([CH3:32])[CH3:28])[CH:22]=[CH:21][CH:20]=2)=[O:16]

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 22310940Methyl 4-hydroxy-1H-indole-2-carboxylate

Product 1

HCID 66841425methyl 4-(2-propoxy)-1H-indole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

DEAD (0.227 ml, 1.47 mmol) is slowly added to a solution of 4-Hydroxy-1H-indole-2-carboxylic acid methyl ester 75 (200 mg, 1.05 mmol), triphenylphosphine (384 mg, 1.47 mmol) and isopropanol (0.108 ml, 1.43 mmol) in 2 ml of THF. Stirring is continued for 20 minutes and the solvent is then evaporated. The crude mixture is purified by chromatography on silicagel using cyclohexane/EtOAc (9/1).

Workup

  1. customthe solvent is then evaporated
  2. customThe crude mixture is purified by chromatography on silicagel

Sources & evidence

ORD record
ord-8e8adc0a2ea547438e9e1c375e5ba549
Source dataset
uspto-grants-2010_12
Patent number
US07858781B2

Reaction notes

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