Potassium Carbonate → 5-{5-[3-(3-Hydroxy-propoxy)-phenylamino]-2-methyl-phenyl}-2-methylsulfanyl-4-pyridin-3-yl-thiophene-3-carbonitrile

HRID 478186

Reaktionsgleichung

Reaktionsgleichung von HRID 478186
[OH:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[CH:10]=[CH:11][C:12]([CH3:30])=[C:13]([C:15]3[S:19][C:18]([S:20][CH3:21])=[C:17]([C:22]#[N:23])[C:16]=3[C:24]3[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=3)[CH:14]=2)[CH:5]=[CH:6][CH:7]=1.Br[CH2:32][CH2:33][CH2:34][OH:35].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[OH:35][CH2:34][CH2:33][CH2:32][O:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[CH:10]=[CH:11][C:12]([CH3:30])=[C:13]([C:15]3[S:19][C:18]([S:20][CH3:21])=[C:17]([C:22]#[N:23])[C:16]=3[C:24]3[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=3)[CH:14]=2)[CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 123083-Bromo-1-propanolHCID 220190375-[5-(3-Hydroxy-phenylamino)-2-methyl-phenyl]-2-methylsulfanyl-4-pyridin-3-yl-thiophene-3-carbonitrile

Produkt 1

HCID 220190305-{5-[3-(3-Hydroxy-propoxy)-phenylamino]-2-methyl-phenyl}-2-methylsulfanyl-4-pyridin-3-yl-thiophene-3-carbonitrileAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 5-[5-(3-hydroxy-phenylamino)-2-methyl-phenyl]-2-methylsulfanyl-4-pyridin-3-yl-thiophene-3-carbonitrile (330 mg, 0.77 mmol) in DMF (anhydrous, 5 mL) was added 3-bromo-propan-1-ol (214 mL, 1.54 mmol). The reaction was stirred at 70° C. in the presence of excess K2CO3 overnight then cooled to ambient temperature and partitioned between water and DCM. The mixture was extracted with DCM (30 ml×3) and the combined organic layers were dried over Na2SO4 and concentrated in vacuo. Purification by chromatography (2% MeOH-DCM) afforded desired product (370 mg, 99%). 1H NMR (CDCl3): δ8.6(d, 1H), 8.5 (d, 1H), 8.1 (s, 1H), 7.7 (d, 1H), 7.4 (s, 1H), 7.3-7.2 (m, 3H), 7.0 (d, 1H), 6.6 (d, 1H), 4.1 (t, 2H), 3.9 (t, 2H), 2.7 (s, 3H), 2.0 (m, 2H), 1.5 (s, 3H)

Aufarbeitung

  1. custompartitioned between water and DCM
  2. extractionThe mixture was extracted with DCM (30 ml×3)
  3. dry with materialthe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customPurification by chromatography (2% MeOH-DCM)

Quellen und Nachweise

ORD-Eintrag
ord-7be151711567424e9b92275701409212
Quelldatensatz
uspto-grants-2003_11
Patentnummer
US06642227B2

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