Iodoethane → HCID 66772095, compound

HRID 1645333Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:16][CH3:17])[C:8]2[C:13]([CH:14]=1)=[C:12]([OH:15])[CH:11]=[CH:10][CH:9]=2)=[O:5])[CH3:2].[H-].[Na+].[CH2:20](I)[CH3:21]>CN(C=O)C.CCOC(C)=O>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:16][CH3:17])[C:8]2[C:13]([CH:14]=1)=[C:12]([O:15][CH2:20][CH3:21])[CH:11]=[CH:10][CH:9]=2)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 1-ethyl-4-hydroxy-1H-indole-2-carboxylic acid ethyl ester (100 mg, 0.43 mmol) and NaH (13 mg, 0.52 mmol) was stirred in DMF (3 mL) for 10 min. Ethyl iodide (80 mg, 0.52 mmol) diluted in 1 mL of DMF was added and placed in a sealed tube. The reaction mixture was heated to 120° C. via microwave for a period of 15 min. The reaction mixture was taken up in 100 mL of EtOAc and washed with 100 mL of 0.1N hydrochloric acid, brine (50 mL), and dried over anhydrous sodium sulfate. The solvent was removed to produce 4-ethoxy-1-ethyl-1H-indole-2-carboxylic acid ethyl ester (112 mg, 100% yield) as brown oil. This material was diluted in 2 mL of methanol and 2 mL of 1N NaOH and placed in a sealed tube. The reaction mixture was heated to 120° C. via microwave for 15 min. The reaction mixture was diluted in 100 mL of EtOAc and washed with 50 mL of 1N HCl, 50 mL of brine, dried over anhydrous sodium sulfate. The solvent was removed to afford 4-ethoxy-1-ethyl-1H-indole-2-carboxylic acid (100 mg, 100% yield) as a white solid. LCMS for C13H15NO3 calcd. (m/e) 233, observed 234 (M+H).

Workup

additionwas added
customplaced in a sealed tube
washwashed with 100 mL of 0.1N hydrochloric acid, brine (50 mL)
dry with materialdried over anhydrous sodium sulfate
customThe solvent was removed

Sources & evidence

ORD record: ord-37f9d51793cc47aaabda8908d9fe3f9e
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08124766B2

Reaction notes

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