Sodium Carbonate → HCID 178505812, Verbindung

HRID 45895

Reaktionsgleichung

Reaktionsgleichung von HRID 45895
C([N:8](CC1C=CC=CC=1)[C:9]1[CH:14]=[CH:13][C:12]([F:15])=[C:11]([C:16]2[C:20]([C:21]3[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=3)=[CH:19][NH:18][N:17]=2)[C:10]=1[F:27])C1C=CC=CC=1.[F:35][C:36]1[CH:43]=[CH:42][C:41]([F:44])=[CH:40][C:37]=1[CH:38]=O.C([BH3-])#N.[Na+].C([O-])([O-])=O.[Na+].[Na+]>CO.C(O)(=O)C.O>[F:35][C:36]1[CH:43]=[CH:42][C:41]([F:44])=[CH:40][C:37]=1[CH2:38][NH:8][C:9]1[CH:14]=[CH:13][C:12]([F:15])=[C:11]([C:16]2[C:20]([C:21]3[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=3)=[CH:19][NH:18][N:17]=2)[C:10]=1[F:27]

Komponenten

8

Edukt 4

HCID 10340Sodium CarbonateHCID 1376632,5-DifluorobenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 178505869HCID 178505869, Verbindung

Produkt 1

HCID 178505812HCID 178505812, VerbindungAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel2×

Versuchsvorschrift

Dibenzyl-[2,4-difluoro-3-(4-pyridin-4-yl-1H-pyrazol-3-yl)-phenyl]-amine (prepared as described in Example 22) (150 mg, 0.551 mmol) was dissolved in a 1:1:1 mixture of methanol, acetic acid and water (18 mL). Freshly distilled 2,5-difluorobenzaldehyde (0.180 mL, 1.653 mmol, 3 eq) was then added, followed by sodiumcyanoborohydride (2.424 mmol, 4.4 eq) and the mixture was stirred at room temperature for 5 hours. It was then poured into water, basified to pH 10 by addition of a saturated aqueous solution of Na2CO3 and extracted with ethyl acetate (3×30 mL). The combine dorganic layers were washed with brine, dried over Na2SO4 and evaporated to dryness. The crude product was purified by flash chromatography on silica gel (DCM/MeOH 96:4) to give 124 mg (85%) of (2,5-difluoro-benzyl)-[2,4-difluoro-3-(4-pyridin-4-yl-1H-pyrazol-3-yl)-phenyl]-amine a white solid.

Aufarbeitung

  1. extractionextracted with ethyl acetate (3×30 mL)
  2. washThe combine dorganic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. customevaporated to dryness
  5. customThe crude product was purified by flash chromatography on silica gel (DCM/MeOH 96:4)

Quellen und Nachweise

ORD-Eintrag
ord-9749bc73eb07490ca8a3512677aea7ec
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541575B2

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