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Sodium Bicarbonate → N-(3,4-Dimethoxybenzyl)-5-(3,5-dimethylphenyl)-2-(1-methyl-1H-pyrazol-4-yl)nicotinamide

HRID 1675938
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1675938
Cl[C:2]1[N:21]=[CH:20][C:19]([C:22]2[CH:27]=[C:26]([CH3:28])[CH:25]=[C:24]([CH3:29])[CH:23]=2)=[CH:18][C:3]=1[C:4]([NH:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([O:16][CH3:17])[CH:9]=1)=[O:5].[CH3:30][N:31]1[CH:35]=[C:34](B2OC(C)(C)C(C)(C)O2)[CH:33]=[N:32]1.C(=O)(O)[O-].[Na+]>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>[CH3:17][O:16][C:10]1[CH:9]=[C:8]([CH:13]=[CH:12][C:11]=1[O:14][CH3:15])[CH2:7][NH:6][C:4](=[O:5])[C:3]1[CH:18]=[C:19]([C:22]2[CH:27]=[C:26]([CH3:28])[CH:25]=[C:24]([CH3:29])[CH:23]=2)[CH:20]=[N:21][C:2]=1[C:34]1[CH:33]=[N:32][N:31]([CH3:30])[CH:35]=1
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Komponenten

5

Edukt 3

HCID 516892Sodium BicarbonateHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 585390332-Chloro-N-(3,4-dimethoxybenzyl)-5-(3,5-dimethylphenyl)nicotinamide

Produkt 1

HCID 25224401N-(3,4-Dimethoxybenzyl)-5-(3,5-dimethylphenyl)-2-(1-methyl-1H-pyrazol-4-yl)nicotinamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 178418397
HCID 178418397, Verbindung
Katalysator

Versuchsvorschrift

To a solution of 2-chloro-N-(3,4-dimethoxybenzyl)-5-(3,5-dimethylphenyl)nicotinamide (1-3, 50.0 mg, 0.122 mmol)) and 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (25.3 mg, 0.122 mmol) in dioxanes (3 mL) was added tetrakis(triphenylphosphine)palladium(0) (7.03 mg, 6.08 μmol) and 2 N aqueous sodium bicarbonate solution (0.304 mL, 0.608 mmol). Under microwave heating the deoxygenated mixture was held at 160° C. for 1 h. The reaction mixture was filtered and concentrated to dryness. A solid residue was triturated with ethyl acetate (4 mL), collected by filtration, washed with water (10 mL) and air dried to afford N-(3,4-dimethoxybenzyl)-5-(3,5-dimethylphenyl)-2-(1-methyl-1H-pyrazol-4-yl)nicotinamide (1-4). 1H NMR (300 MHz, DMSO) δ 9.09 (t, 1H, J=5.8 Hz), 8.87 (d, 1H, J=1.8 Hz), 7.92 (d, 1H, J=1.8 Hz), 7.82 (d, 1H, J=9.8 Hz), 7.39 (s, 2H), 7.06 (s, 1H), 6.92 (m, 3H), 4.29 (d, 2H, J=5.3 Hz), 3.74 (m, 6H), 3.32 (s, 3H), 2.35 (s, 3H). HRMS m/z (M+H) 457.2242 found, 457.2234 required.

Aufarbeitung

  1. temperatureUnder microwave heating the deoxygenated mixture
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated to dryness
  4. customA solid residue was triturated with ethyl acetate (4 mL)
  5. filtrationcollected by filtration
  6. washwashed with water (10 mL) and air
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-f0c641c19dce47228119cef85acf41b6
Quelldatensatz
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08003797B2

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