Dimethyl Sulfate → 2-[Bis(cyclopropylmethyl)amino]-6-fluoropyridine-3-carbaldehyde

HRID 1911796Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1911796
[OH-].[Na+].FC(F)(F)C1C=C(C=C(C(F)(F)F)C=1)CN([CH2:15][C:16]1[C:17]([N:23]([CH2:28][CH:29]2[CH2:31][CH2:30]2)[CH2:24][CH:25]2[CH2:27][CH2:26]2)=[N:18][C:19]([F:22])=[CH:20][CH:21]=1)C1NN=NN=1.S(OC)(OC)(=O)=[O:42]>O.ClCCl.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH:25]1([CH2:24][N:23]([CH2:28][CH:29]2[CH2:31][CH2:30]2)[C:17]2[C:16]([CH:15]=[O:42])=[CH:21][CH:20]=[C:19]([F:22])[N:18]=2)[CH2:27][CH2:26]1

Komponenten

7

Edukt 3

HCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 178505795HCID 178505795, Verbindung

Produkt 1

HCID 587957962-[Bis(cyclopropylmethyl)amino]-6-fluoropyridine-3-carbaldehydeAusbeute 125,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To sodium hydroxide (33.6 mg, 0.8 mmol) stirred in water (2 mL) was added (3-{[(3,5-bis-trifluoromethyl-benzyl)-(1H-tetrazol-5-yl)-amino]-methyl}-6-fluoro-pyridine-2-yl)-bis-cyclopropylmethyl-amine (222 mg, 0.4 mmol) in dichloromethane (5 mL). After stirring for 15 minutes, dimethyl sulfate (0.05 mL, 0.44 mmol) and tetrabutylammonium bromide (7.5 mg, 0.0176 mmol) was added and the solution was left to stir at room temperature for 1 hour. The solution was extracted with dichloromethane (2×15 mL). The combined organic layers were washed with water and brine, dried over sodium sulfate, filtered and then concentrated under vacuum to give an orange oily product. Purification by silica gel chromatography and eluting with 30% ethyl acetate in hexanes afforded the title compound as an orange oil (124.6 mg, yield: 56%).

Aufarbeitung

  1. waitthe solution was left
  2. stirringto stir at room temperature for 1 hour
  3. extractionThe solution was extracted with dichloromethane (2×15 mL)
  4. washThe combined organic layers were washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customto give an orange oily product
  9. customPurification by silica gel chromatography
  10. washeluting with 30% ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-3e4758b1b8b84e1583ec88404d498996
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08604055B2

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