Acetic Acid → HCID 135494373, Verbindung

HRID 1633511Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1633511
[F:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:20][C:21]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][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:35](C)C=O>>[Cl:29][C:26]1[CH:27]=[CH:28][C:23]([C:21]2[N:35]=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[OH:19])[CH:10]=[C:9]([C:4]3[CH:5]=[CH:6][C:7]([F:8])=[C:2]([F:1])[CH:3]=3)[CH:20]=2)=[CH:24][CH:25]=1

Komponenten

4

Edukt 3

HCID 176Acetic AcidHCID 6228DimethylformamideHCID 18679597HCID 18679597, Verbindung

Produkt 1

HCID 135494373HCID 135494373, Verbindung

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 3-(3,4-difluorophenyl)-1-(2-hydroxyphenyl)-5-(4-chlorophenyl)-1,5-pentanedione on Wang resin (2.0 g, 1.76 mmol), NH4OAc (0.80 g), and AcOH (1.0 mL) in dimethylformamide (20 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, and lyophilized to give 2-[6-(4-chloro-phenyl)-4-(3,4-difluoro-phenyl)-pyridin-2-yl]-phenol; mp 146-148 ° C.; 1H NMR (DMSO-d6) d 6.75 (m, 1 H), 7.00 (m, 2 H), 7.35 (m, 2 H), 7.57 (m, 1 H), 7.69 (d, J=8.6 Hz, 2 H), 7.95 (d, J =8.6 Hz, 1 H), 8.18 (d, J=8.6 Hz, 2 H), 8.32 (m, 2 H), 14.00 (s, 1 H); IR (KBr) 1606 cm−1; MS [M+1] m/z=394. Anal. calcd for C23H14ClF2NO: C, 70.15; H, 3.58; N, 3.50; Found: C, 69.98; H, 3.51; N, 1.80.

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

Quellen und Nachweise

ORD-Eintrag
ord-1b5c65f8d2c04bddb555b7dd513fbf89
Quelldatensatz
uspto-grants-2003_01
Patentnummer
US06503917B1

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