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Potassium Acetate → 1,1-dimethylethyl 7-(2-methyl-1-{[(2-methylpropyl)-oxy]carbonyl}-1H-imidazo[4,5-b]pyridine-6-yl)-2,3-dihydro-1,4-benzoxazepine-4(5H)carboxylate

HRID 241148
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 241148
Br[C:2]1[CH:3]=[C:4]2[N:10]([C:11]([O:13][CH2:14][CH:15]([CH3:17])[CH3:16])=[O:12])[C:9]([CH3:18])=[N:8][C:5]2=[N:6][CH:7]=1.[CH3:19][C:20]([O:23][C:24]([N:26]1[CH2:32][C:31]2[CH:33]=[C:34](B(O)O)[CH:35]=[CH:36][C:30]=2[O:29][CH2:28][CH2:27]1)=[O:25])([CH3:22])[CH3:21].C([O-])(=O)C.[K+]>O1CCOCC1.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]>[CH3:18][C:9]1[N:10]([C:11]([O:13][CH2:14][CH:15]([CH3:17])[CH3:16])=[O:12])[C:4]2[C:5]([N:8]=1)=[N:6][CH:7]=[C:2]([C:34]1[CH:35]=[CH:36][C:30]3[O:29][CH2:28][CH2:27][N:26]([C:24]([O:23][C:20]([CH3:21])([CH3:19])[CH3:22])=[O:25])[CH2:32][C:31]=3[CH:33]=1)[CH:3]=2
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 517044Potassium AcetateHCID 59604707(4-(Tert-butoxycarbonyl)-2,3,4,5-tetrahydrobenzo[f][1,4]oxazepin-7-yl)boronic acidHCID 66820076isobutyl 6-bromo-2-methyl-1H-imidazo[4,5-b]pyridine-1-carboxylate

Produkt 1

HCID 668201401,1-dimethylethyl 7-(2-methyl-1-{[(2-methylpropyl)-oxy]carbonyl}-1H-imidazo[4,5-b]pyridine-6-yl)-2,3-dihydro-1,4-benzoxazepine-4(5H)carboxylateAusbeute 33 %

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

A mixture of isobutyl 6-bromo-2-methyl-1H-imidazo[4,5-b]pyridine-1-carboxylate (2.2 g, 7.1 mmol) (reagent preparation 19), (4-{[(1,1-dimethylethyl)oxy]carbonyl}-2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)boronic acid (2.7 g, 9.2 mmol, example 1, step 2), potassium acetate (2.8 g, 28.3 mmol), and dichloro[1,1-bis(diphenylphosphino]-ferrocenepalladium (II) dichloromethane adduct (0.78 g, 1.1 mmol) in dioxane (50 ml) was stirred at 95° C. under nitrogen for 29 h. The mixture was cooled to room temperature, filtered through celite, and the filter cake was washed with ethyl acetate (100 ml). The filtrate was concentrated and purified by column chromatography on silica (0-100% ethyl acetate in hexanes) to give 1,1-dimethylethyl 7-(2-methyl-1-{[(2-methylpropyl)oxy]carbonyl}-1H-imidazo[4,5-b]pyridine-6-yl)-2,3-dihydro-1,4-benzoxazepine-4(5H)carboxylate (1.1 g, 33% yield) as a yellow solid. 1H NMR (400 MHz, CDCl3): 8.74 (d, 1H), 8.39 (s, 1H), 7.47 (d, 1H), 7.43 (s, 1H), 7.14 (d, 1H), 4.50 (s, 2H), 4.34 (d, 2H), 4.12 (m, 2H), 3.88 (m, 2H), 2.96 (s, 3H), 2.22 (m, 1H), 1.42 (s, 9H), 1.21 (d, 6H); MS (EI) for C26H32N4O5: 481 (MH+).

Aufarbeitung

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationfiltered through celite
  3. washthe filter cake was washed with ethyl acetate (100 ml)
  4. concentrationThe filtrate was concentrated
  5. custompurified by column chromatography on silica (0-100% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-e93b912058444f7db294ad4e8015fbd3
Quelldatensatz
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08648066B2

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