Sodium Bicarbonate → Methyl 2-fluoro-5-[{4-[(4-fluorophenyl)ethynyl]benzyl)-(hexyl)amino]benzoate

HRID 551967Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 551967
[F:1][C:2]1[CH:11]=[CH:10][C:9]([NH:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[F:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]#[C:27][C:28]2[CH:35]=[CH:34][C:31]([CH:32]=O)=[CH:30][CH:29]=2)=[CH:22][CH:21]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>ClCCCl>[F:1][C:2]1[CH:11]=[CH:10][C:9]([N:12]([CH2:32][C:31]2[CH:30]=[CH:29][C:28]([C:27]#[C:26][C:23]3[CH:22]=[CH:21][C:20]([F:19])=[CH:25][CH:24]=3)=[CH:35][CH:34]=2)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Komponenten

6

Edukt 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 43715358Methyl 2-fluoro-5-(hexylamino)benzoateHCID 454901144-[2-(4-Fluorophenyl)ethynyl]benzaldehyde

Produkt 1

HCID 57554486Methyl 2-fluoro-5-[{4-[(4-fluorophenyl)ethynyl]benzyl)-(hexyl)amino]benzoateAusbeute 32 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of methyl 2-fluoro-5-(hexylamino)benzoate (270 mg; 1.07 mmol) and 4-[(4-fluorophenyl)ethynyl]benzaldehyde (358 mg; 1.60 mmol, intermediate which may be obtained according to methods disclosed in EP03103780.7) in anhydrous DCE (15 mL) was added sodium triacetoxyborohydride (678 mg; 3.20 mmol) at rt. The reaction mixture was then heated at 50° C. for 14 h. It was then poured into a solution of saturated NaHCO3 and extracted twice with DCM. The combined organic phases were then washed with brine, dried over MgSO4, filtrated and concentrated. The crude brown oil (652 mg) was purified by preparative HPLC using a X-Terra column to give 158 mg (32%) of the title compound as a beige powder. HPLC, Rt: 6.01 min (purity: 96.5%), LC/MS, M+(ESI): 462.2, 1H NMR: (CDCl3) δ: 7.46 (m, 2H), 7.41 (d, J=8.3 Hz, 2H), 7.37 (m, 1H), 7.13 (d, J=7.9 Hz, 2H), 6.94-7.05 (m, 4H), 4.52 (s, 2H), 3.90 (s, 3H), 3.42 (t, J=7.7 Hz, 2H), 1.56 (m, 2H), 1.26 (m, 6H), 0.85 (t, J=6.6 Hz, 3H).

Aufarbeitung

  1. extractionextracted twice with DCM
  2. washThe combined organic phases were then washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltrated
  5. concentrationconcentrated
  6. customThe crude brown oil (652 mg) was purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-bdbd0bd98cfe4bb886f4b6f6e72d5cc1
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07947851B2

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