Dichloromethane → 5-tert-butyl-4-chloro-2-methyl-2H-pyrazole-3-carboxylic acid [3-(4-methoxy-benzylamino)-5-(2-trifluoromethyl-phenyl)-pyrazin-2-yl]-amide

HRID 1191212Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1191212
Br[C:2]1[N:3]=[C:4]([NH:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=2)[C:5]([NH:8][C:9]([C:11]2[N:12]([CH3:21])[N:13]=[C:14]([C:17]([CH3:20])([CH3:19])[CH3:18])[C:15]=2[Cl:16])=[O:10])=[N:6][CH:7]=1.[F:32][C:33]([F:44])([F:43])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1B(O)O.C([O-])([O-])=O.[K+].[K+].C(Cl)Cl>CN(C=O)C.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].O.C1(C)C=CC=CC=1>[CH3:31][O:30][C:27]1[CH:28]=[CH:29][C:24]([CH2:23][NH:22][C:4]2[C:5]([NH:8][C:9]([C:11]3[N:12]([CH3:21])[N:13]=[C:14]([C:17]([CH3:19])([CH3:18])[CH3:20])[C:15]=3[Cl:16])=[O:10])=[N:6][CH:7]=[C:2]([C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=3[C:33]([F:44])([F:43])[F:32])[N:3]=2)=[CH:25][CH:26]=1

Komponenten

9

Edukt 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 27343872-(Trifluoromethyl)benzeneboronic acidHCID 866574125-tert-butyl-4-chloro-2-methyl-2H-pyrazole-3-carboxylic acid [5-bromo-3-(4-methoxy-benzylamino)-pyrazin-2-yl]-amide

Produkt 1

HCID 674122355-tert-butyl-4-chloro-2-methyl-2H-pyrazole-3-carboxylic acid [3-(4-methoxy-benzylamino)-5-(2-trifluoromethyl-phenyl)-pyrazin-2-yl]-amide

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of 5-tert-butyl-4-chloro-2-methyl-2H-pyrazole-3-carboxylic acid [5-bromo-3-(4-methoxy-benzylamino)-pyrazin-2-yl]-amide (87 mg, 0.17 mmol), 2-trifluoromethyl-phenylboronic acid (36 mg, 0.19 mmol), in DMF (0.5 mL), toluene (2 mL) and water (2 mL), K2CO3 (33 mg, 0.23 mmol) was added. The resulting solution was placed under Ar and (dppf)PdCl2.DCM (14 mg, 0.02 mmol) was added. The resulting mixture was stirred at 100° C. overnight. The organic layer was separated, dried (Na2SO4) and concentrated. The residue obtained was purified on silica (20:80-100:0 EtOAc:hexane) to yield 5-tert-butyl-4-chloro-2-methyl-2H-pyrazole-3-carboxylic acid [3-(4-methoxy-benzylamino)-5-(2-trifluoromethyl-phenyl)-pyrazin-2-yl]-amide. Mass Spectrum (LCMS, ESI pos.): Calculated for C28H28ClF3N6O: 573.1 (M+H); Measured: 573.3.

Aufarbeitung

  1. customThe organic layer was separated
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customThe residue obtained
  5. customwas purified on silica (20:80-100:0 EtOAc:hexane)

Quellen und Nachweise

ORD-Eintrag
ord-587db7fd21164b0083260115fef617f5
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08680098B2

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