Acetic Acid → HCID 135544070, Verbindung

HRID 1934522Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1934522
[F:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:20][C:21]([C:23]2[CH:32]=[CH:31][C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH:24]=2)=O)[CH2:10][C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[OH:19])=O)[CH:5]=[CH:6][C:7]=1[F:8].CC(O)=O.C[N:38](C)C=O>>[F:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:20]=[C:21]([C:23]3[CH:32]=[CH:31][C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[CH:24]=3)[N:38]=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[OH:19])[CH:10]=2)[CH:5]=[CH:6][C:7]=1[F:8]

Komponenten

4

Edukt 3

HCID 176Acetic AcidHCID 6228DimethylformamideHCID 18679589HCID 18679589, Verbindung

Produkt 1

HCID 135544070HCID 135544070, Verbindung

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 3-(3,4-difluorophenyl)-1-(2-hydroxyphenyl)-5-(naphthalen-2-yl)-1,5-pentanedione on Wang resin (2.0 g, 1.76 mmol), NH4OAc (1.0 g), and AcOH (1.5 mL) in dimethylformamide (40 mL) was heated at 100° C. for 18 h. The resin was filtered, and washed with dimethylformamide (×2) and alternating MeOH and CH2Cl2 (×5), and dried under high vacuum overnight. The dried resin was treated with 50% TFA/CH2Cl2 (15 mL) for 1 h. After filtration of the reaction mixture, the filtrate was concentrated to dryness. The residue was repeatedly dissolved in CH2Cl2 (10 mL) and concentrated to remove traces of TFA. Purification by flash chromatography gave 2-[4-(3,4-difluoro-phenyl)-6-naphthalen-2-yl-pyridin-2-yl]-phenol; mp 165-167° C.; 1H NMR (DMSO-d6) d 6.99 (m, 2 H), 7.38 (m, 1 H), 7.65 (m, 4 H), 8.06 (m, 4 H), 8.24 (d, J=6.8 Hz, 1 H), 8.42 (m, 2 H), 8.49 (d, J=1.2 Hz, 1 H), 8.74 (s, 1 H), 14.35 (s, 1 H); IR (KBr) 1602 cm −1; MS [M+H]+ m/z=410. Anal. calcd for C27H17F2NO: C, 79.21; H, 4.19; N, 3.42; Found: C, 79.33; H, 4.19; N, 3.22.

Aufarbeitung

  1. filtrationThe resin was filtered
  2. washwashed with dimethylformamide (×2)
  3. customdried under high vacuum overnight
  4. additionThe dried resin was treated with 50% TFA/CH2Cl2 (15 mL) for 1 h
  5. filtrationAfter filtration of the reaction mixture
  6. concentrationthe filtrate was concentrated to dryness
  7. dissolutionThe residue was repeatedly dissolved in CH2Cl2 (10 mL)
  8. concentrationconcentrated
  9. customto remove traces of TFA
  10. customPurification by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-bd8ec9a0bbd842ac9f6ef13d205946bc
Quelldatensatz
uspto-grants-2002_05
Patentnummer
US06384058B1

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