Dichloromethane → (1-cyclohexyl-2-(5-(3-(methoxymethyl)phenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-3-ylamino)-1H-benzo[d]imidazol-5-yl)methanol

HRID 2068292

Reaktionsgleichung

Reaktionsgleichung von HRID 2068292
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[N:6]=[C:5]2[NH:19][C:20]1[N:24]([CH:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)[C:23]2[CH:31]=[CH:32][C:33]([CH2:35][OH:36])=[CH:34][C:22]=2[N:21]=1.[CH3:37][O:38][CH2:39][C:40]1[CH:41]=[C:42](B(O)O)[CH:43]=[CH:44][CH:45]=1.ClCCl>>[CH:25]1([N:24]2[C:23]3[CH:31]=[CH:32][C:33]([CH2:35][OH:36])=[CH:34][C:22]=3[N:21]=[C:20]2[NH:19][C:5]2[C:4]3[C:8](=[CH:9][CH:10]=[C:2]([C:44]4[CH:43]=[CH:42][CH:41]=[C:40]([CH2:39][O:38][CH3:37])[CH:45]=4)[CH:3]=3)[N:7]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:16])([CH3:17])[CH3:18])[N:6]=2)[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]1

Komponenten

4

Edukt 3

HCID 6344DichloromethaneHCID 38258553-(Methoxymethyl)benzeneboronic acidHCID 67255070(2-(5-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-3-ylamino)-1-cyclohexyl-1H-benzo[d]imidazol-5-yl)methanol

Produkt 1

HCID 67253467(1-cyclohexyl-2-(5-(3-(methoxymethyl)phenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-3-ylamino)-1H-benzo[d]imidazol-5-yl)methanolAusbeute 103,3 %

Versuchsvorschrift

In a small microwave tube added (2-(5-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-3-ylamino)-1-cyclohexyl-1H-benzo[d]imidazol-5-yl)methanol (52.4 mg, 0.0000918 mol), 3-(methoxymethyl)phenylboronic acid (25.1 mg, 0.000151 mol) and (1,1′-bis(diphenylphosphino)ferrocene)dichloropalladium(II) complexed with dichloromethane (1:1) (16.2 mg, 0.0000198 mol). The tube was flushed with argon and the contents were dissolved in 1,4-dioxane (1.5 mL) and 2 M sodium carbonate (150 uL). The reaction was microwaved for 10 minutes at 120° C. The cooled reaction mixture was filtered through a syringe filter and the filter washed 3× with methanol. The combined eluents were concentrated to yield 58 mg of crude product used directly in the next step.

Aufarbeitung

  1. customThe tube was flushed with argon
  2. dissolutionthe contents were dissolved in 1,4-dioxane (1.5 mL)
  3. customThe reaction was microwaved for 10 minutes at 120° C
  4. customThe cooled reaction mixture
  5. filtrationwas filtered through a syringe
  6. filtrationfilter
  7. washthe filter washed 3× with methanol
  8. concentrationThe combined eluents were concentrated

Quellen und Nachweise

ORD-Eintrag
ord-82ec1458f9df4af3844055c27a8e0239
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08293923B2

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