Tributylphosphine → 5-Allyloxy-1-[(2-thiophen-3-yl)ethyl]-1h-indole-2-carboxylic acid ethyl ester

HRID 434017Notes

Reaction equation

HRID 434017 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([O:15][CH2:16][CH:17]=[CH2:18])=[CH:10][CH:9]=2)=[O:5])[CH3:2].[S:19]1[CH:23]=[CH:22][C:21]([CH2:24][CH2:25]O)=[CH:20]1.C(P(CCCC)CCCC)CCC>C1COCC1>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:25][CH2:24][C:21]2[CH:22]=[CH:23][S:19][CH:20]=2)[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([O:15][CH2:16][CH:17]=[CH2:18])=[CH:10][CH:9]=2)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 13831TributylphosphineHCID 83731Thiophene-3-ethanolHCID 13286893Ethyl 5-[(prop-2-en-1-yl)oxy]-1H-indole-2-carboxylate

Product 1

HCID 120944655-Allyloxy-1-[(2-thiophen-3-yl)ethyl]-1h-indole-2-carboxylic acid ethyl esterYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To solution of 5-allyloxyindole-2-carboxylic acid ethyl ester (1.0 g, 4.08 mmol) in THF (10 mL) was added azodicarboxylic acid bis[dimethylamide] (TMAD; 1.4 g, 8.15 mmol). After stirring at room temperature for 20 min, 2-(3-thienyl)ethanol (0.78 g, 6.12 mmol) was added followed by the addition of tributyl phosphine (1.65 g, 8.15 mmol). After stirring at room temperature for 18 h, the reaction was partitioned between ethyl acetate and water. The organic layer was washed with brine and dried over Na2SO4. Purification by flash colunmn chromatography (silica gel, EtOAc/hexanes) yielded the desired product as an oil (1.36 g, 94%).

Workup

  1. stirringAfter stirring at room temperature for 18 h
  2. customthe reaction was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. customPurification by flash colunmn chromatography (silica gel, EtOAc/hexanes)

Sources & evidence

ORD record
ord-2659ad643eac46948a902f9d8b56e9fb
Source dataset
uspto-grants-2003_12
Patent number
US06670388B1

Reaction notes

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