Sodium Carbonate → HCID 58464845, Verbindung

HRID 2089423Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2089423
[NH2:1][C:2]1[C:3]([C:9]([NH:11][C:12]2[CH:13]=[N:14][N:15]([CH3:17])[CH:16]=2)=[O:10])=[N:4][C:5](Br)=[CH:6][CH:7]=1.[N:18]1([C:24]2[CH:25]=[C:26](B(O)O)[CH:27]=[CH:28][CH:29]=2)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.C([O-])([O-])=O.[Na+].[Na+].C([O-])(=O)C.[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].C(#N)C>[NH2:1][C:2]1[C:3]([C:9]([NH:11][C:12]2[CH:13]=[N:14][N:15]([CH3:17])[CH:16]=2)=[O:10])=[N:4][C:5]([C:26]2[CH:27]=[CH:28][CH:29]=[C:24]([N:18]3[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]3)[CH:25]=2)=[CH:6][CH:7]=1

Komponenten

7

Edukt 4

HCID 10340Sodium CarbonateHCID 517044Potassium AcetateHCID 17982644[3-(Piperidin-1-yl)phenyl]boronic acidHCID 58464823HCID 58464823, Verbindung

Produkt 1

HCID 58464845HCID 58464845, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a microwave reaction vial was added 317 from Example 317 (150 mg, 0.51 mmol), 3-(piperidin-1-yl)phenylboronic acid (312 mg, 1.52 mmol), dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) (41 mg, 0.051 mmol), a 1M solution of Na2CO3 (0.76 mL), a 1M solution of potassium acetate (0.76 mL) and acetonitrile (11 mL). The mixture was irradiated to 120° C. with a microwave for 30 min and cooled to room temperature. It was filtered through Celite and thoroughly washed with methylene chloride. The filtrate was concentrated and the residue was purified via flash chromatography, 0 to 7% methanol in methylene chloride (with 1% ammonium hydroxide). The product was further purified via reverse phase HPLC to afford 318. 1H NMR (400 MHz, DMSO) δ 10.34 (s, 1H), 8.07 (s, 1H), 7.86 (d, J=8.7 Hz, 1H), 7.71 (s, 1H), 7.59-7.43 (m, 2H), 7.34-7.17 (m, 2H), 7.03-6.84 (m, 3H), 3.83 (s, 3H), 3.26-3.18 (m, 4H), 1.73-1.48 (m, 7H). MS (ESI) m/z: 377.2 [M+H+].

Aufarbeitung

  1. customTo a microwave reaction
  2. customThe mixture was irradiated to 120° C. with a microwave for 30 min
  3. filtrationIt was filtered through Celite
  4. washthoroughly washed with methylene chloride
  5. concentrationThe filtrate was concentrated
  6. customthe residue was purified via flash chromatography, 0 to 7% methanol in methylene chloride (with 1% ammonium hydroxide)
  7. customThe product was further purified via reverse phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-c0b2708c4fc34ba4a5a84ad6b5a3cdbc
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08436001B2

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