Sodium Carbonate → HCID 56597463, Verbindung

HRID 2174952Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2174952
[C:1]([N:3]=[C:4]1[N:19]([CH3:20])[C:7]2[CH:8]=[N:9][C:10]3[CH:11]=[CH:12][C:13](B(O)O)=[CH:14][C:15]=3[C:6]=2[N:5]1[C:21]1[CH:26]=[CH:25][C:24]([C:27]([C:30]#[N:31])([CH3:29])[CH3:28])=[CH:23][CH:22]=1)#[N:2].Br[C:33]1[CH:34]=[C:35]([NH:41][S:42]([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)(=[O:44])=[O:43])[C:36]([O:39][CH3:40])=[N:37][CH:38]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C>[C:1]([N:3]=[C:4]1[N:19]([CH3:20])[C:7]2[CH:8]=[N:9][C:10]3[CH:11]=[CH:12][C:13]([C:33]4[CH:34]=[C:35]([NH:41][S:42]([C:45]5[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=5)(=[O:44])=[O:43])[C:36]([O:39][CH3:40])=[N:37][CH:38]=4)=[CH:14][C:15]=3[C:6]=2[N:5]1[C:21]1[CH:26]=[CH:25][C:24]([C:27]([C:30]#[N:31])([CH3:29])[CH3:28])=[CH:23][CH:22]=1)#[N:2]

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 59859943HCID 59859943, VerbindungHCID 86683444HCID 86683444, Verbindung

Produkt 1

HCID 56597463HCID 56597463, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
111 °C

Versuchsvorschrift

To the stirred solution (2-(cyanoimino)-1-(4-(2-cyanopropan-2-yl)phenyl)-3-methyl-2,3-dihydro-1H-imidazo[4,5-c]quinolin-8-yl)boronic acid (0.390 mmol) in dry DMF (5 ml) was added N-(5-bromo-2-methoxypyridin-3-yl)benzenesulfonamide (0.39 mmol) followed by catalyst palladium dichlorobis triphenylphosphine (0.039 mmol). Saturated solution of sodium carbonate (0.780 mmol) was added to it and the resulting solution was heated at 111° C. for 8 minutes in microwave. Solvent was removed and the crude material was extracted with EtOAc, washed with brine several times and dried over anhydrous Na2SO4. The solvent was evaporated and the crude solid was purified (silica gel column, CHCl3/MeOH as eluent) to obtain the title compound. 1H NMR (300 MHz, DMSO-d6): δ 10.01 (s, 1H), 9.23 (s, 1H), 8.20 (d, J=8.7 Hz, 1H), 7.88 (s, 4H), 7.84 (m, 1H), 7.70 (m, 4H), 7.56 (m, 3H), 6.83 (s, 1H), 3.92 (s, 3H), 3.58 (s, 3H), 1.81 (s, 6H); MS (m/z): 629 (M+1)+.

Aufarbeitung

  1. customSolvent was removed
  2. extractionthe crude material was extracted with EtOAc
  3. washwashed with brine several times
  4. dry with materialdried over anhydrous Na2SO4
  5. customThe solvent was evaporated
  6. customthe crude solid was purified (silica gel column, CHCl3/MeOH as eluent)

Quellen und Nachweise

ORD-Eintrag
ord-a71377fb55b44619a289c61bb2a88f44
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09062046B2

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