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Water → 5-[4-chloro-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-nicotinic acid ethyl ester

HRID 1693706
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1693706
Br[C:2]1[C:3]([Cl:19])=[C:4]2[CH:10]=[CH:9][N:8]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[C:5]2=[N:6][CH:7]=1.[CH2:20]([O:22][C:23]([C:25]1[CH:26]=[N:27][CH:28]=[C:29](B2OC(C)(C)C(C)(C)O2)[CH:30]=1)=[O:24])[CH3:21].ClCCl.O>C(#N)C.C1(C)C=CC=CC=1.C(=O)(O)[O-].[Na+]>[CH2:20]([O:22][C:23](=[O:24])[C:25]1[CH:30]=[C:29]([C:2]2[C:3]([Cl:19])=[C:4]3[CH:10]=[CH:9][N:8]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[C:5]3=[N:6][CH:7]=2)[CH:28]=[N:27][CH:26]=1)[CH3:21]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 962WaterHCID 6344DichloromethaneHCID 3816953Ethyl 5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3-carboxylateHCID 575376665-Bromo-4-chloro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo(2,3-b)pyridine

Produkt 1

HCID 575375885-[4-chloro-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-nicotinic acid ethyl ester
Ausbeute 56,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 1140TolueneLösungsmittelHCID 6342AcetonitrileLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

1.59 g (4.40 mmol) of 5-bromo-4-chloro-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridine, 1.482 g (5.35 mmol) of 3-(ethoxycarbonyl)pyridine-5-boronic acid pinacol ester and 181 mg (0.22 mmol) of (1,1′-bis(diphenylphosphino)ferrocenepalladium(II)-dichloride dichloromethane adduct were dissolved in a mixture of 7 mL of acetonitrile, 7 mL of toluene and 8 mL of a saturated aqueous solution of sodium bicarbonate. The resulting mixture was heated to 110° C. in a closed vial for 15 h. The resulting mixture was distributed between dichloromethane and water. The aqueous phase was separated and extracted three times with dichloromethane and the once with ethyl acetate. The ethyl acetate phase was washed with brine and combined with the other organic phases, dried over sodium sulfate and evaporated. The resulting crude was purified by flash chromatography on silica gel using a gradient of ethyl acetate in hexanes to afford 1.0703 g (2.48 mmol, 56%) of 5-[4-chloro-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-nicotinic acid ethyl ester as a pale yellow oil. 1H-NMR [500 MHz, d6-DMSO] δ: 9.15 (d, 1H), 8.97 (d, 1H), 8.41 (m, 1H), 8.40 (m, 1H), 7.89 (d, 1H), 5.69 (s, 2H), 4.38 (q, 2H), 3.55 (t, 2H), 1.35 (t, 3H), 0.84 (t, 2H), −0.08 (s, 9H); MS [MH+] m/z: 432+434.

Aufarbeitung

  1. customThe aqueous phase was separated
  2. extractionextracted three times with dichloromethane
  3. washThe ethyl acetate phase was washed with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customThe resulting crude was purified by flash chromatography on silica gel using a gradient of ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-0e0f4ba479414ce988f2b50623931f96
Quelldatensatz
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08158647B2

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