Dichloromethane → 5-[7-(1-methyl-cyclohexanecarbonyl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-thiophene-2-carboxylic acid

HRID 547482Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 547482
OB(O)[C:3]1[S:7][C:6]([C:8]([OH:10])=[O:9])=[CH:5][CH:4]=1.Br[C:13]1[N:14]=[C:15]2[C:21]([C:22]([C:24]3([CH3:30])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)=[O:23])=[CH:20][N:19]([CH2:31][O:32][CH2:33][CH2:34][Si:35]([CH3:38])([CH3:37])[CH3:36])[C:16]2=[N:17][CH:18]=1.C(=O)([O-])[O-].[K+].[K+].C(Cl)Cl>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:30][C:24]1([C:22]([C:21]2[C:15]3[C:16](=[N:17][CH:18]=[C:13]([C:3]4[S:7][C:6]([C:8]([OH:10])=[O:9])=[CH:5][CH:4]=4)[N:14]=3)[N:19]([CH2:31][O:32][CH2:33][CH2:34][Si:35]([CH3:36])([CH3:38])[CH3:37])[CH:20]=2)=[O:23])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]1

Komponenten

8

Edukt 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 27798075-Boronothiophene-2-carboxylic acidHCID 57829583[2-bromo-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-(1-methyl-cyclohexyl)-methanone

Produkt 1

HCID 578295975-[7-(1-methyl-cyclohexanecarbonyl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-thiophene-2-carboxylic acidAusbeute 50,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A mixture of 5-(dihydroxyboryl)-2-thiophene-carboxylic acid (1.0 g, 5.4 mmol), [2-bromo-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-(1-methyl-cyclohexyl)-methanone (2.2 g, 4.9 mmol), potassium carbonate (2.0 g, 15 mmol), and Pd(dppf)Cl2.CH2Cl2 (0.400 g, 0.489 mmol) in 12 mL of 1,4-dioxane and 3 mL of water was stirred at 120° C. in a microwave for 40 min. The resulting red suspension was partitioned between 60 mL of ethyl acetate and 100 mL of water, and the aqueous layer was extracted with three 60 mL portions of ethyl acetate. The combined organic layers were dried over MgSO4, filtered and concentrated to a residue. Column chromatography (0->50% EtOAc/hexanes) afforded 1.24 g (46%) of 5-[7-(1-methyl-cyclohexanecarbonyl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-thiophene-2-carboxylic acid as a brown solid.

Aufarbeitung

  1. customThe resulting red suspension was partitioned between 60 mL of ethyl acetate and 100 mL of water
  2. extractionthe aqueous layer was extracted with three 60 mL portions of ethyl acetate
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to a residue

Quellen und Nachweise

ORD-Eintrag
ord-e2c4f2cf268a4717a933f22b82635a9a
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07939531B2

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