Cesium carbonate → HCID 44556110, Verbindung

HRID 336395Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 336395
[CH3:1][CH:2]([C:4]1[CH:5]=[C:6]([C:10]2[N:15]3[N:16]=[C:17]([NH2:19])[N:18]=[C:14]3[CH:13]=[CH:12][CH:11]=2)[CH:7]=[CH:8][CH:9]=1)[CH3:3].Cl[C:21]1[CH:26]=[CH:25][N:24]=[C:23]([CH3:27])[CH:22]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:3][CH:2]([C:4]1[CH:5]=[C:6]([C:10]2[N:15]3[N:16]=[C:17]([NH:19][C:21]4[CH:26]=[CH:25][N:24]=[C:23]([CH3:27])[CH:22]=4)[N:18]=[C:14]3[CH:13]=[CH:12][CH:11]=2)[CH:7]=[CH:8][CH:9]=1)[CH3:1]

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 5813924-Chloro-2-methylpyridineHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 445561185-[3-(Propan-2-yl)phenyl][1,2,4]triazolo[1,5-a]pyridin-2-amine

Produkt 1

HCID 44556110HCID 44556110, VerbindungAusbeute 54,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
210 °C

Versuchsvorschrift

A suspension of 5-[3-(propan-2-yl)phenyl][1,2,4]triazolo[1,5-a]pyridin-2-amine (88.9 mg, 0.352 mmol, 1.00 equiv), 4-chloro-2-methylpyridine (53.9 mg, 0.423 mmol, 1.20 equiv), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (17.6 mg, 0.0369 mmol, 0.105 equiv), cesium carbonate (237 mg, 0.727 mmol, 2.06 equiv), and tris(dibenzylideneacetone)dipalladium(0) (10.0 mg, 0.0109 mmol, 0.0310 equiv) in N,N-dimethylformamide (2 mL) was heated in the microwave to 210° C. for 20 min. The reaction mixture was concentrated in vacuo (˜1 mm Hg). The resulting residue was partitioned between saturated aqueous sodium chloride solution (5 mL) and ethyl acetate (5 mL). The organic was separated, and the aqueous phase was extracted with ethyl acetate (2×5 mL). The collected organic was dried over anhydrous sodium sulfate, filtered, and concentrated. Purification by preparative HPLC yielded a white solid (65.5 mg, 54%). 1H NMR (400 MHz, DMSO-d6), δ: 10.13 (s, 1H), 8.16 (m, 1H), 7.95 (s, 1H), 7.83 (m, 1H), 7.63-7.72 (m, 2H), 7.44-7.55 (m, 4H), 7.25 (dd, J=7.1, 1.3 Hz, 1H), 3.03 (m, 1H), 2.37 (s, 3H), 1.30 (d, J=6.9 Hz, 6H).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in vacuo (˜1 mm Hg)
  2. customThe resulting residue was partitioned between saturated aqueous sodium chloride solution (5 mL) and ethyl acetate (5 mL)
  3. customThe organic was separated
  4. extractionthe aqueous phase was extracted with ethyl acetate (2×5 mL)
  5. dry with materialThe collected organic was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-76d5142d0195410e97bd1a92c6261b7f
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889673B2

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