Potassium Carbonate → Tert-butyl 4-(2-(1-acetylindolin-5-yl)ethyl)piperazine-1-carboxylate

HRID 383820

Reaction equation

[N:1]1([C:7]([OH:9])=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[C:16]([N:19]1[C:27]2[C:22](=[CH:23][C:24]([C:28](=O)[CH2:29]Br)=[CH:25][CH:26]=2)[CH2:21][CH2:20]1)(=[O:18])[CH3:17]>C(#N)C>[C:16]([N:19]1[C:27]2[C:22](=[CH:23][C:24]([CH2:28][CH2:29][N:4]3[CH2:5][CH2:6][N:1]([C:7]([O:9][C:22]([CH3:27])([CH3:23])[CH3:21])=[O:8])[CH2:2][CH2:3]3)=[CH:25][CH:26]=2)[CH2:21][CH2:20]1)(=[O:18])[CH3:17]

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of piperazine-1-carboxylic acid tent-butyl ester (0.750 g, 4.03 mmol) in dry acetonitrile (20 mL) grounded potassium carbonate (0.486 mL, 8.05 mmol) was added followed by the product mixture from Example 38a (1.134 g) and the reaction was heated at 70° C. under argon over night. The acetonitrile was evaporated and DCM and water was added. The layers were separated and the aq phase was extracted with DCM (3×). The combined organic phases were dried (Na2SO4), filtered and evaporated. The crude mixture was purified by flash chromatography (heptane/EtOAc 75/25 to 0/100) to give 0.823 g (55%) of the title compound.

Workup

additionwas added
customThe acetonitrile was evaporated
additionDCM and water was added
customThe layers were separated
extractionthe aq phase was extracted with DCM (3×)
dry with materialThe combined organic phases were dried (Na2SO4)
filtrationfiltered
customevaporated
customThe crude mixture was purified by flash chromatography (heptane/EtOAc 75/25 to 0/100)

Sources & evidence

ORD record: ord-f0b72abc57aa416888c498f997519efe
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08367676B2

Linked notes

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