Potassium Carbonate → 1,1,1-trifluoro-4-(2-methoxy-5-pyridin-3-ylphenyl)-4-methyl-2-(1H-pyrrolo[2,3-c]pyridin-2-ylmethyl)pentan-2-ol

HRID 400673Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 400673
Br[C:2]1[CH:3]=[CH:4][C:5]([O:28][CH3:29])=[C:6]([C:8]([CH3:27])([CH3:26])[CH2:9][C:10]([CH2:16][C:17]2[NH:25][C:20]3=[CH:21][N:22]=[CH:23][CH:24]=[C:19]3[CH:18]=2)([OH:15])[C:11]([F:14])([F:13])[F:12])[CH:7]=1.B1([C:36]2[CH:41]=[CH:40][CH:39]=[N:38][CH:37]=2)OCCCO1.C(=O)([O-])[O-].[K+].[K+]>COCCOC.CO.CN(C=O)C.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:12][C:11]([F:14])([F:13])[C:10]([CH2:16][C:17]1[NH:25][C:20]2=[CH:21][N:22]=[CH:23][CH:24]=[C:19]2[CH:18]=1)([OH:15])[CH2:9][C:8]([C:6]1[CH:7]=[C:2]([C:36]2[CH:37]=[N:38][CH:39]=[CH:40][CH:41]=2)[CH:3]=[CH:4][C:5]=1[O:28][CH3:29])([CH3:27])[CH3:26]

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 41980053-(1,3,2-Dioxaborinan-2-yl)pyridineHCID 469390184-(5-bromo-2-methoxyphenyl)-1,1,1-trifluoro-4-methyl-2-(1H-pyrrolo[2,3-c]pyridin-2-ylmethyl)pentan-2-ol

Produkt 1

HCID 600264501,1,1-trifluoro-4-(2-methoxy-5-pyridin-3-ylphenyl)-4-methyl-2-(1H-pyrrolo[2,3-c]pyridin-2-ylmethyl)pentan-2-olAusbeute 48 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 8857Ethyl AcetateLösungsmittelHCID 86594022DME MeOH DMFLösungsmittel

Versuchsvorschrift

A mixture of 4-(5-bromo-2-methoxyphenyl)-1,1,1-trifluoro-4-methyl-2-(1H-pyrrolo[2,3-c]pyridin-2-ylmethyl)pentan-2-ol (188 mg, 0.4 mmol), pyridine 3-boronic acid 1,3-propanediol cyclic ester (89 mg, 0.6 mmol), potassium carbonate (K2CO3; 166 mg, 1.2 mmol), and Pd(PPh3)4 (46.2 mg, 0.04 mmol) in 3.0 mL of DME-MeOH-DMF (1:1.5:0.5) was microwaved for 20 minutes at 120° C., cooled to room temperature, diluted with 20 mL of ethyl acetate and filtered through diatomaceous earth. The filtrate was washed with 5 mL of 1.0 M aqueous sodium hydroxide solution, water, and brine, dried over magnesium sulfate, and concentrated in vacuo. The residue was purified by silica gel chromatography to yield 90 mg (48% yield) of the title compound as a white foam.

Aufarbeitung

  1. customwas microwaved for 20 minutes at 120° C.
  2. filtrationfiltered through diatomaceous earth
  3. washThe filtrate was washed with 5 mL of 1.0 M aqueous sodium hydroxide solution, water, and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-b2319c32d2214ed39b9f0eb83982e198
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08741897B2

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