Potassium Carbonate → 2-(4-isopropylphenyl)-N-[(S)-(1-methyl-1H-1,2,3-triazol-4-yl)(5-propylpyridin-2-yl)methyl]acetamide

HRID 877345

Reaktionsgleichung

Reaktionsgleichung von HRID 877345
Br[C:2]1[CH:3]=[CH:4][C:5]([C@H:8]([C:22]2[N:23]=[N:24][N:25]([CH3:27])[CH:26]=2)[NH:9][C:10](=[O:21])[CH2:11][C:12]2[CH:17]=[CH:16][C:15]([CH:18]([CH3:20])[CH3:19])=[CH:14][CH:13]=2)=[N:6][CH:7]=1.[CH2:28](B(O)O)[CH2:29][CH3:30].C([O-])([O-])=O.[K+].[K+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH:18]([C:15]1[CH:16]=[CH:17][C:12]([CH2:11][C:10]([NH:9][C@@H:8]([C:22]2[N:23]=[N:24][N:25]([CH3:27])[CH:26]=2)[C:5]2[CH:4]=[CH:3][C:2]([CH2:28][CH2:29][CH3:30])=[CH:7][N:6]=2)=[O:21])=[CH:13][CH:14]=1)([CH3:20])[CH3:19]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 3510651-Propylboronic acidHCID 67171186N-[(5)-(5-bromopyridin-2-yl)(1-methyl-1H-1,2,3-triazol-4-yl)methyl]-2-(4-isopropylphenyl)acetamide

Produkt 1

HCID 671730222-(4-isopropylphenyl)-N-[(S)-(1-methyl-1H-1,2,3-triazol-4-yl)(5-propylpyridin-2-yl)methyl]acetamideAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Katalysator

Versuchsvorschrift

N-[(S)-(5-bromopyridin-2-yl)(1-methyl-1H-1,2,3-triazol-4-yl)methyl]-2-(4-isopropylphenyl)acetamide (0.075 g, 0.18 mmol) was mixed with n-propylboronic acid (0.04 g, 0.44 mmol), PdCl2(dppf)2 (0.014 g, 0.019 mmol), Ag2O (0.10 g, 0.44 mmol) and K2CO3 (0.073 g, 0.53 mmol) and degassed. THF (3 mL) was added and the mixture was heated in microwave at 130 C for 30 min. The reaction mixture was diluted with EtOAc and filtered through Celite. The solvent was removed and the residue was purified by reverse HPLC to give 2-(4-isopropylphenyl)-N-[(S)-(1-methyl-1H-1,2,3-triazol-4-yl)(5-propylpyridin-2-yl)methyl]acetamide (0.035 g, 51%). ES-MS [M+1]+: 430.1. 1H NMR (CDCl3, 400 MHz) δ 1H NMR (CDCl3, 400 MHz) δ 8.29 (d, J=2.0 Hz, 1H), 7.58 (d, J=6.4 Hz, 1H), 7.45 (dd, J=2.4, 8.0 Hz, 1H), 7.40 (s, 1H), 7.27 (d, J=8.0 Hz, 1H), 7.24-7.19 (ABq, 4H), 6.27 (d, J=7.2 Hz, 1H), 3.98 (s, 3H), 3.62 (s, 2H), 2.94-2.85 (m, J=6.8 Hz, 1H), 2.54 (t, J=7.6 Hz, 2 H), 1.66-1.56 (m, 2H), 1.24 (d, J=6.4 Hz, 6H), 0.93 (t, J=7.2 Hz, 3H). HRMS (ES) [M+1]+ calcd for C23H29N5O: 392.2445. Found: 392.2446.

Aufarbeitung

  1. customdegassed
  2. additionTHF (3 mL) was added
  3. temperaturethe mixture was heated in microwave at 130 C for 30 min
  4. additionThe reaction mixture was diluted with EtOAc
  5. filtrationfiltered through Celite
  6. customThe solvent was removed
  7. customthe residue was purified by reverse HPLC

Quellen und Nachweise

ORD-Eintrag
ord-16f85acb2ad74fb29ac1b1a09f47c603
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08987310B2

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