Cesium carbonate → 3-tert-Butyl-N-(3-{[1-(2,2-diethoxyethyl)-1'-(4-methoxybenzyl)-1H,1'H-3,4'-bipyrazol-5-yl]amino}-4-methylphenyl)benzamide

HRID 1055669Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1055669
[CH2:1]([O:3][CH:4]([O:26][CH2:27][CH3:28])[CH2:5][N:6]1[C:10]([NH2:11])=[CH:9][C:8]([C:12]2[CH:13]=[N:14][N:15]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=3)[CH:16]=2)=[N:7]1)[CH3:2].Br[C:30]1[CH:31]=[C:32]([NH:37][C:38](=[O:49])[C:39]2[CH:44]=[CH:43][CH:42]=[C:41]([C:45]([CH3:48])([CH3:47])[CH3:46])[CH:40]=2)[CH:33]=[CH:34][C:35]=1[CH3:36].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:45]([C:41]1[CH:40]=[C:39]([CH:44]=[CH:43][CH:42]=1)[C:38]([NH:37][C:32]1[CH:31]=[CH:30][C:35]([CH3:36])=[C:34]([NH:11][C:10]2[N:6]([CH2:5][CH:4]([O:3][CH2:1][CH3:2])[O:26][CH2:27][CH3:28])[N:7]=[C:8]([C:12]3[CH:13]=[N:14][N:15]([CH2:17][C:18]4[CH:19]=[CH:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=4)[CH:16]=3)[CH:9]=2)[CH:33]=1)=[O:49])([CH3:48])([CH3:46])[CH3:47]

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 866909601-(2,2-Diethoxyethyl)-1'-(4-methoxybenzyl)-1H,1'H-3,4'-bipyrazol-5-amineHCID 86690964N-(3-Bromo-4-methylphenyl)-3-tert-butylbenzamide

Produkt 1

HCID 896999063-tert-Butyl-N-(3-{[1-(2,2-diethoxyethyl)-1'-(4-methoxybenzyl)-1H,1'H-3,4'-bipyrazol-5-yl]amino}-4-methylphenyl)benzamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

200 mg (0.44 mmol, purity 85%) of the compound from Example 2A and 199 mg (0.57 mmol) of the compound of Example 46A in 2.18 ml of 1,4-dioxane were degassed with argon. 9.9 mg (0.044 mmol) of palladium(II) acetate, 38.3 mg (0.066 mmol) of xantphos and 431 mg (1.32 mmol) of caesium carbonate were added and the mixture was heated in a microwave oven (Biotage Initiator, with Dynamic Field Tuning) at 150° C. for 30 min. The reaction was then filtered through kieselguhr and the filtrate was concentrated. The residue was subjected to flash-chromatography on silica gel (mobile phase dichloromethane/ethyl acetate 1:1). The product fractions were concentrated under reduced pressure and the residue was dried. This gave 180 mg (63% of theory) of the title compound.

Aufarbeitung

  1. filtrationThe reaction was then filtered through kieselguhr
  2. concentrationthe filtrate was concentrated
  3. concentrationThe product fractions were concentrated under reduced pressure
  4. customthe residue was dried

Quellen und Nachweise

ORD-Eintrag
ord-756f2d63695e467f961867c24c10b138
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09394309B2

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