Water → 2-amino-5-[1-(2-oxo-2-piperidin-1-ylethyl)-1H-pyrazol-4-yl]pyridine-3-carbaldehyde

HRID 241406Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 241406
[NH2:1][C:2]1[C:7]([CH:8]=[O:9])=[CH:6][C:5](I)=[CH:4][N:3]=1.[N:11]1([C:17](=[O:33])[CH2:18][N:19]2[CH:23]=[C:22](B3OC(C)(C)C(C)(C)O3)[CH:21]=[N:20]2)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.C(=O)([O-])[O-].[Na+].[Na+].O>CN(C)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>[NH2:1][C:2]1[C:7]([CH:8]=[O:9])=[CH:6][C:5]([C:22]2[CH:21]=[N:20][N:19]([CH2:18][C:17](=[O:33])[N:11]3[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]3)[CH:23]=2)=[CH:4][N:3]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 177501772-Amino-5-iodopyridine-3-carbaldehydeHCID 534020131-(piperidin-1-yl)-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)ethanone

Produkt 1

HCID 866648052-amino-5-[1-(2-oxo-2-piperidin-1-ylethyl)-1H-pyrazol-4-yl]pyridine-3-carbaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

5.1 200 mg (0.806 mmol) of 2-amino-5-iodopyridine-3-carbaldehyde and 501 mg (1.570 mmol) of 1-piperidin-1-yl-2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazol-1-yl]ethanone are dissolved in 4 ml of N,N-dimethylformamide in an argon-filled microwave vessel, and 2.5 ml (5 mmol) of 2M sodium carbonate solution and 93.2 mg (0.081 mmol) of tetrakis(triphenylphosphine)palladium(0) are added. The reaction solution is irradiated with microwaves for 30 min at 120° C. in the Biotage SmithSynthesizer. The reaction mixture is cooled to room temperature, water is added, and the mixture is filtered. The filtrate is extracted three times with ethyl acetate, and the combined organic phases are washed 2× with water, dried using sodium sulfate, and evaporated to dryness. The oily residue is purified by means of RP-HPLC, giving 2-amino-5-[1-(2-oxo-2-piperidin-1-ylethyl)-1H-pyrazol-4-yl]pyridine-3-carbaldehyde as yellowish powder; ESI-MS [M+H]+ 314.2.

Aufarbeitung

  1. additionfilled microwave vessel
  2. customThe reaction solution is irradiated with microwaves for 30 min at 120° C. in the Biotage SmithSynthesizer
  3. filtrationthe mixture is filtered
  4. extractionThe filtrate is extracted three times with ethyl acetate
  5. washthe combined organic phases are washed 2× with water
  6. customdried
  7. customevaporated to dryness
  8. customThe oily residue is purified by means of RP-HPLC

Quellen und Nachweise

ORD-Eintrag
ord-2743e2f9d5c64b6da7d259413087769d
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08648201B2

Notizen zur Reaktion

Wird geladen…