Diisopropylamine → S-1-(4-Fluorophenyl)-1H-indazol-5-yl benzothioate

HRID 13123

Reaktionsgleichung

Reaktionsgleichung von HRID 13123
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13](I)=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1.[C:18]([OH:26])(=[S:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.CC1C=NC2C(C=1C)=CC=C1C=2N=CC(C)=C1C.C(NC(C)C)(C)C>C1(C)C=CC=CC=1.CCOC(C)=O.[I+].[Cu+]>[C:18](=[O:26])([S:25][C:13]1[CH:12]=[C:11]2[C:16](=[CH:15][CH:14]=1)[N:8]([C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)[N:9]=[CH:10]2)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Komponenten

8

Edukt 4

HCID 7912DiisopropylamineHCID 742653,4,7,8-Tetramethyl-1,10-phenanthrolineHCID 592511281-(4-fluorophenyl)-5-iodo-1H-indazoleHCID 178526132HCID 178526132, Verbindung

Produkt 1

HCID 59339848S-1-(4-Fluorophenyl)-1H-indazol-5-yl benzothioateAusbeute 20 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178505377HCID 178505377, VerbindungKatalysatorHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 1-(4-fluorophenyl)-5-iodo-1H-indazole (103e, 0.224 g, 0.66 mmol), thiobenzoic acid (0.093 ml, 0.79 mmol), 3,4,7,8-tetramethyl-1,10-phenantroline (0.031 g, 0.13 mmol) and N,N-diisopropylamine (0.220 ml, 1.32 mmol) in toluene (2.5 ml) was added copper(I) iodine (2.245 μl, 0.07 mmol). The resulting mixture was stirred at 110 C O/N. The reaction mixture was cooled to r.t. diluted with EtOAc and washed with water. The organic phase was the dried the solvent evaporated and then purified on HPLC. The relevant fractions were collected freezdried to give 45 mg of product (20% yield) which was analysed by LC/MS.

Aufarbeitung

  1. washwashed with water
  2. customdried the solvent
  3. customevaporated
  4. custompurified on HPLC
  5. customThe relevant fractions were collected freezdried

Quellen und Nachweise

ORD-Eintrag
ord-5b1dc549e4134f18b2f42ea77cf3f868
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728030B2

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