Ammonium Chloride → 7-bromo-N-(3-cyclopropyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide

HRID 79492

Reaktionsgleichung

Reaktionsgleichung von HRID 79492
[Br:1][C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]([O:13]CC)=O)=[CH:9][N:10]=[C:4]2[CH:3]=1.[CH:16]1([C:19]2[C:27]3[C:26]([NH2:28])=[CH:25][CH:24]=[CH:23][C:22]=3[N:21]([CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[C:32]([CH3:36])[N:31]=3)[N:20]=2)[CH2:18][CH2:17]1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[Cl-].[NH4+]>C1COCC1.CC(O)C>[Br:1][C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]([NH:28][C:26]3[CH:25]=[CH:24][CH:23]=[C:22]4[C:27]=3[C:19]([CH:16]3[CH2:18][CH2:17]3)=[N:20][N:21]4[CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[C:32]([CH3:36])[N:31]=3)=[O:13])=[CH:9][N:10]=[C:4]2[CH:3]=1

Komponenten

7

Edukt 4

HCID 25517Ammonium ChlorideHCID 2733832Lithium HexamethyldisilazideHCID 672592723-cyclopropyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazole-4-amineHCID 67260906Ethyl 7-bromoimidazo[1,2-a]pyridine-3-carboxylate

Produkt 1

HCID 532618947-bromo-N-(3-cyclopropyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamideAusbeute 88,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3776IsopropanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-13 °C

Versuchsvorschrift

A mixture of ethyl 7-bromoimidazo[1,2-a]pyridine-3-carboxylate (0.54 g, 2.0 mmol) and 3-cyclopropyl-1-((6-methylpyridin-2-yl)methyl)-1H-indazol-4-amine (0.56 g, 2.0 mmol; prepared as in Example 65, steps A1-A3) in THF (10 mL) was cooled to −13° C. using an ice/water/MeOH bath. A solution of 1.0M lithium bis(trimethylsilyl)amide (4.4 mL, 4.4 mmol) was added over 5 minutes keeping the internal temperature below −10° C. The mixture was stirred at −10° C. for 10 minutes, warmed to ambient temperature and concentrated to give an oily residue. The residue was dissolved using IPA (10 mL) and treated with a 10% aqueous ammonium chloride solution (20 mL) to give a slurry which was stirred overnight. The slurry was filtered to collect the solid which was dried under vacuum to give the product (0.89 g). MS (ES+APCI) m/z=501.0 (M+H).

Aufarbeitung

  1. customthe internal temperature below −10° C
  2. temperaturewarmed to ambient temperature
  3. concentrationconcentrated
  4. customto give an oily residue
  5. dissolutionThe residue was dissolved
  6. customto give a slurry which
  7. stirringwas stirred overnight
  8. filtrationThe slurry was filtered
  9. customto collect the solid which
  10. customwas dried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-c289c9c51f47468283e99122c3c3cff6
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841455B2

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