Tert-butyl 4-(2-bromo-4-fluorophenyl)-4-(((4'-cyano-5-(trifluoromethyl)biphenyl-3-yl)methoxy)methyl)piperidine-1-carboxylate → 3'-(((4-(2-Bromo-4-fluorophenyl)piperidin-4-yl)methoxy)methyl)-5'-(trifluoromethyl)biphenyl-4-carbonitrile

HRID 391465

Reaktionsgleichung

Reaktionsgleichung von HRID 391465
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1([CH2:22][O:23][CH2:24][C:25]2[CH:26]=[C:27]([C:35]3[CH:40]=[CH:39][C:38]([C:41]#[N:42])=[CH:37][CH:36]=3)[CH:28]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:30]=2)[CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11][CH2:10]1>ClCCl.FC(F)(F)C(O)=O>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1([CH2:22][O:23][CH2:24][C:25]2[CH:26]=[C:27]([C:35]3[CH:40]=[CH:39][C:38]([C:41]#[N:42])=[CH:37][CH:36]=3)[CH:28]=[C:29]([C:31]([F:34])([F:32])[F:33])[CH:30]=2)[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1

Komponenten

4

Edukt 1

HCID 58993540Tert-butyl 4-(2-bromo-4-fluorophenyl)-4-(((4'-cyano-5-(trifluoromethyl)biphenyl-3-yl)methoxy)methyl)piperidine-1-carboxylate

Produkt 1

HCID 589934843'-(((4-(2-Bromo-4-fluorophenyl)piperidin-4-yl)methoxy)methyl)-5'-(trifluoromethyl)biphenyl-4-carbonitrileAusbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

A solution of tert-butyl 4-(2-bromo-4-fluorophenyl)-4-(((4′-cyano-5-(trifluoromethyl)biphenyl-3-yl)methoxy)methyl)piperidine-1-carboxylate (50 mg, 0.077 mmol) in dichloromethane (0.5 mL) and trifluoroacetic acid (2 mL) was stirred at ambient temperature for 3 hours. The reaction was evaporated to dryness and the resulting residue was purified by chromatography on silica with gradient of methanol/dichloromethane of 2% to 10%. The product 3′-(((4-(2-bromo-4-fluorophenyl)piperidin-4-yl)methoxy)methyl)-5′-(trifluoromethyl)biphenyl-4-carbonitrile (29 mg, 69% yield) was obtained as a clear oil. 1H-NMR (CDCl3, 400 MHz) δ 7.74 (d, J=6.8 Hz, 2H), 7.68 (s, 1H), 7.58 (d, J=6.7 Hz, 2H), 7.36 (s, 1H), 7.33 (s, 1H), 7.22-7.33 (m, 2H), 7.03 (m, 1H), 4.49 (s, 2H), 3.88 (s, 2H), 3.25 (m, 2H), 2.94 (m, 2H), 2.85 (m, 2H), 2.23 (m, 2H). Mass spec.: 547.12 (M+H), HPLC (method 5) 3.37 min.

Aufarbeitung

  1. customThe reaction was evaporated to dryness
  2. customthe resulting residue was purified by chromatography on silica with gradient of methanol/dichloromethane of 2% to 10%

Quellen und Nachweise

ORD-Eintrag
ord-4fda3ee25d844e3694928a651a4f0a53
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08383821B2

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