2-(Dimethylamino)ethanol → 6-(2-Dimethylamino-ethoxy)-1-isopropyl-1H-indole-4-carboxylic acid methyl ester

HRID 873372Notes

Reaction equation

HRID 873372 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:6]2[CH:7]=[CH:8][N:9]([CH:15]([CH3:17])[CH3:16])[C:10]=2[CH:11]=[C:12]([OH:14])[CH:13]=1)=[O:4].[CH3:18][N:19]([CH3:23])[CH2:20][CH2:21]O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[CH3:1][O:2][C:3]([C:5]1[C:6]2[CH:7]=[CH:8][N:9]([CH:15]([CH3:17])[CH3:16])[C:10]=2[CH:11]=[C:12]([O:14][CH2:21][CH2:20][N:19]([CH3:23])[CH3:18])[CH:13]=1)=[O:4]

Participants

6

Reactant 4

HCID 79022-(Dimethylamino)ethanolHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 674654646-hydroxy-1-isopropyl-1H-indole-4-carboxylic acid methyl ester

Product 1

HCID 674665686-(2-Dimethylamino-ethoxy)-1-isopropyl-1H-indole-4-carboxylic acid methyl esterYield 60.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cooled (0° C.) mixture of 6-hydroxy-1-isopropyl-1H-indole-4-carboxylic acid methyl ester (700 mg, 3 mmol), 2-dimethylamino-ethanol (320 mg, 3.60 mmol) and PPh3 (948 mg, 3.60 mmol) in THF (10 mL) was added DEAD (620 mg, 3.60 mmol) and stirred for 16 h at RT. Reaction mixture was concentrated under reduced pressure and the residue was purified by column chromatography by eluting with 2% MeOH in chloroform to afford the title compound (550 mg, 60%) as colorless gum. LCMS (ES+): m/z=305.36 [M+H].

Workup

  1. temperatureTo a cooled
  2. customReaction mixture
  3. concentrationwas concentrated under reduced pressure
  4. customthe residue was purified by column chromatography
  5. washby eluting with 2% MeOH in chloroform

Sources & evidence

ORD record
ord-aa355f7567e145348e366c6b9210b99b
Source dataset
uspto-grants-2015_03
Patent number
US08975291B2

Reaction notes

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