1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 3-{4-[6-(4-tert-butylphenylcarbamoyl)-1H-indol-2-yl]-3,5-dimethylphenyl}-propionic acid methyl ester

HRID 1514959Notes

Reaction equation

[CH3:1][O:2][C:3]([CH2:5][CH2:6][C:7]1[CH:12]=[C:11]([CH3:13])[C:10]([C:14]2[NH:15][C:16]3[C:21]([CH:22]=2)=[CH:20][CH:19]=[C:18]([C:23](O)=[O:24])[CH:17]=3)=[C:9]([CH3:26])[CH:8]=1)=[O:4].[C:27]([C:31]1[CH:37]=[CH:36][C:34]([NH2:35])=[CH:33][CH:32]=1)([CH3:30])([CH3:29])[CH3:28].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>C1COCC1>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][C:7]1[CH:8]=[C:9]([CH3:26])[C:10]([C:14]2[NH:15][C:16]3[C:21]([CH:22]=2)=[CH:20][CH:19]=[C:18]([C:23](=[O:24])[NH:35][C:34]2[CH:36]=[CH:37][C:31]([C:27]([CH3:30])([CH3:29])[CH3:28])=[CH:32][CH:33]=2)[CH:17]=3)=[C:11]([CH3:13])[CH:12]=1

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 2-[4-(2-methoxycarbonylethyl)-2,6-dimethylphenyl]-1H-indole-6-carboxylic acid (100 mg, 280 μmol), 4-tert-butylaniline (45 μL, 290 μmol), EDCI (82 mg, 430 μmol) and HOBT (42 mg, 310 μmol) in THF (10 mL) was heated in a microwave apparatus at 150° C. for 3 h. The solvent was removed under reduced pressure and the residue was chromatographed using a 10-60% gradient of heptane/ethyl acetate to give 3-{4-[6-(4-tert-butylphenylcarbamoyl)-1H-indol-2-yl]-3,5-dimethylphenyl}-propionic acid methyl ester. MS (m/z) 484.3 (M+1); Retention time=1.50 min (Method 10).

Workup

customThe solvent was removed under reduced pressure
customthe residue was chromatographed

Sources & evidence

ORD record: ord-feb4078d47484e6c8533c345e239c38e
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08222248B2

Reaction notes

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