Potassium Phosphate, Tribasic → HCID 67017338, Verbindung

HRID 1842040Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1842040
Br[C:2]1[CH:9]=[C:8]([S:10]([N:13]2[C:22]3[C:17](=[CH:18][C:19]([C:23]4[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=4)=[CH:20][CH:21]=3)[CH2:16][C:15]([CH3:34])([CH3:33])[CH2:14]2)(=[O:12])=[O:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].BrC1[CH:37]=[C:38]2[C:43](=CC=1)NCC(C)(C)C2.BrC1C=C(S(Cl)(=O)=O)C=CC=1C#N.ClC1C=C(N2C3C(=CC(C4C=CC(C(F)(F)F)=CC=4)=CC=3)C(C)(C)CC2)C=CC=1C1NC(=O)ON=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.C1(B(O)O)CC1>C1(C)C=CC=CC=1.O.C(OCC)(=O)C>[CH:43]1([C:2]2[CH:9]=[C:8]([S:10]([N:13]3[C:22]4[C:17](=[CH:18][C:19]([C:23]5[CH:28]=[CH:27][C:26]([C:29]([F:30])([F:31])[F:32])=[CH:25][CH:24]=5)=[CH:20][CH:21]=4)[CH2:16][C:15]([CH3:33])([CH3:34])[CH2:14]3)(=[O:11])=[O:12])[CH:7]=[CH:6][C:3]=2[C:4]#[N:5])[CH2:38][CH2:37]1

Komponenten

11

Edukt 7

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 2760897Cyclopropylboronic acidHCID 54421415HCID 54421415, VerbindungHCID 67017336HCID 67017336, VerbindungHCID 866651331201684-65-2HCID 135926475HCID 135926475, Verbindung

Produkt 1

HCID 67017338HCID 67017338, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

90 mg 2-Bromo-4-[3,3-dimethyl-6-(4-trifluoromethyl-phenyl)-3,4-dihydro-2H-quinoline-1-sulfonyl]-benzonitrile (derived from 6-Bromo-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline (synthesis described in WO 9629327), 4-(Trifluormethyl)phenyl-ylboronic acid and 3-Bromo-4-cyano-benzenesulfonyl chloride according to the method described for 3-{2-Chloro-4-[4,4-dimethyl-6-(4-trifluoromethyl-phenyl)-3,4-dihydro-2H-quinolin-1-yl]-phenyl}-4H-[1,2,4]oxadiazol-5-one in example 3), 153 mg Potassium phosphate (tribasic heptahydrate) 6 mg tricyclohexylphosphine and 42 mg cyclopropylboronic acid were dissolved in a mixture of 30 ml toluene and 0.6 ml water. An argon stream was bubbled through the reaction mixture for twenty minutes. Then 7.4 mg palladium(II)acetate were added and the reaction mixture stirred under microwave irradiation at 120° C. for one hour. The cooled reaction mixture was diluted with 50 ml ethyl acetate and filtered trough a pad of celite. The filtrate was evaporated and purified by chromatography on silica gel to obtain 73 mg 2-Cyclopropyl-4-[3,3-dimethyl-6-(4-trifluoromethyl-phenyl)-3,4-dihydro-2H-quinoline-1-sulfonyl]-benzonitrile.

Aufarbeitung

  1. customAn argon stream was bubbled through the reaction mixture for twenty minutes
  2. additionThen 7.4 mg palladium(II)acetate were added
  3. customThe cooled reaction mixture
  4. filtrationfiltered trough a pad of celite
  5. customThe filtrate was evaporated
  6. custompurified by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-cada0dc8e60a42c0836481175c93eb75
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08946212B2

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