Sodium Carbonate → 5-[5-(1-Acetyl-piperidin-4-yl)-2-amino-phenyl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

HRID 1043318Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1043318
[C:1]([O:5][C:6]([N:8]1[CH2:13][C:12](B2OC(C)(C)C(C)(C)O2)=[CH:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:23][C:24]1[CH:29]=[CH:28][C:27]([CH:30]2[CH2:35][CH2:34][N:33]([C:36](=[O:38])[CH3:37])[CH2:32][CH2:31]2)=[CH:26][C:25]=1Br.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.CCO.CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:13][C:12]([C:25]2[CH:26]=[C:27]([CH:30]3[CH2:35][CH2:34][N:33]([C:36](=[O:38])[CH3:37])[CH2:32][CH2:31]3)[CH:28]=[CH:29][C:24]=2[NH2:23])=[CH:11][CH2:10][CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 49835909Tert-butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 591285921-[4-(4-Amino-3-bromo-phenyl)-piperidin-1-yl]-ethanone

Produkt 1

HCID 591285815-[5-(1-Acetyl-piperidin-4-yl)-2-amino-phenyl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl esterAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 8857Ethyl AcetateLösungsmittelHCID 21863594Toluene ethanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A solution of 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (as prepared in Example 46, step (b), 0.62 g, 2.02 mmol) and 1-[4-(4-amino-3-bromo-phenyl)-piperidin-1-yl]-ethanone (as prepared in the previous step, 0.20 g, 0.67 mmol) in toluene:EtOH (2:1, 9 mL) was treated with 2.0 M aqueous Na2CO3 (2.7 mL, 5.38 mmol) and was degassed with sonication under Ar. The mixture was heated to 80° C., treated with Pd(PPh3)4 (54 mg, 0.05 mmol), and stirred at 80° C. for 4.5 h. The reaction was cooled to room temperature, diluted with EtOAc, and washed with saturated aqueous NaHCO3. The organic layer was dried over MgSO4 and concentrated in vacuo to afford the title compound (0.25 g, 93%) as an off-white solid. LC-MS (ESI, m/z): Calcd. for C23H33N3O3 422.2 (M+Na). found 422.0.

Aufarbeitung

  1. customwas degassed with sonication under Ar
  2. temperatureThe reaction was cooled to room temperature
  3. washwashed with saturated aqueous NaHCO3
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-3e3e75a1a79a473a9e4cb1220005ddb6
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08557847B2

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