Water → Ethyl 5-[(3,3-dimethylbutanoyl)amino]-1H-indole-2-carboxylate

HRID 1825002

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5]2.C(N(CC)CC)C.[CH3:23][C:24]([CH3:30])([CH3:29])[CH2:25][C:26](Cl)=[O:27].O>C1COCC1>[CH3:23][C:24]([CH3:30])([CH3:29])[CH2:25][C:26]([NH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5]2)=[O:27]

Participants

Conditions

Temperature: 0 °C

Procedure

3.76 g (18.4 mmol) of ethyl 5-amino-1H-indole-2-carboxylate from Example LXI and 2.05 g (2.82 ml, 20.3 mmol) of triethylamine are added to 40 ml of THF. The mixture is cooled to 0° C., and a solution of 2.48 g (2.56 ml, 18.4 mmol) of 3,3-dimethylbutyryl chloride in 20 ml of THF are added. The mixture is stirred at RT for 2 h and, for work-up, poured into water. The pH is adjusted to 7 and the mixture is extracted 3 times with ethyl acetate. The combined organic phases are dried with sodium sulphate, filtered and dried under reduced pressure.

Workup

extractionthe mixture is extracted 3 times with ethyl acetate
dry with materialThe combined organic phases are dried with sodium sulphate
filtrationfiltered
customdried under reduced pressure

Sources & evidence

ORD record: ord-968de18b50634a8bacd41c11cd66fa6a
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07045544B2

Linked notes

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