Tetrabutylammonium Fluoride → HCID 86670548, Verbindung

HRID 874715Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 874715
[NH2:1][C:2]1[C:10]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3([C:21]([F:24])([F:23])[F:22])[N:20]=[N:19]3)=[CH:14][CH:13]=2)([OH:11])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:25]#[C:26][Si](C)(C)C)[CH:8]=2)[N:3]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[NH2:1][C:2]1[C:10]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3([C:21]([F:24])([F:23])[F:22])[N:20]=[N:19]3)=[CH:14][CH:13]=2)([OH:11])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:25]#[CH:26])[CH:8]=2)[N:3]=1

Komponenten

4

Edukt 2

HCID 2724141Tetrabutylammonium FluorideHCID 67167406HCID 67167406, Verbindung

Produkt 1

HCID 86670548HCID 86670548, VerbindungAusbeute 87,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

2-amino-3-{4-[3-(trifluoromethyl)diazirin-3-yl]phenyl}-5-[2-(trimethylsilyl)ethynyl]indol-3-ol (30.5 mg, 0.07 mmol, 1 eq.) was dissolved in THF (5 mL), and 1 M TBAF in THF (0.078 mL, 0.08 mmol, 1.1 eq.) was added. The reaction was stirred at room temperature for 10 minutes. Solvents were then evaporated, and the residue was purified by silica column (DCM/MeOH, 39:1→19:1→9:1→4:1), resulting in 21.8 mg (86%) of the title compound as a yellow solid. 1H NMR (500 MHz, CD3OD) δ 7.45 (d, J=8.5, 2H, Ar—H), 7.33 (dd, J=1.5, 8.0, 1H, Ar—H), 7.23 (d, J=8.2, 2H, Ar—H), 7.10-6.94 (m, 2H, Ar—H). 13C NMR (126 MHz, CD3OD) δ 180.61 (CNH2), 156.96 (C—Ar), 144.65 (C—Ar), 140.97 (C—Ar), 135.30 (C—Ar), 129.59 (C—Ar), 127.92 (d, J=0.90, C—Ar), 127.76 (C—Ar), 127.02 (C—Ar), 123.73 (q, J=273.90, CF3), 117.13 (C—Ar), 116.69 (C—Ar), 84.96 (CCH), 84.23 (Ar—COH), 77.31 (CCH), 29.56 (q, J=40.35, CN2). Exact Mass, 356.09. 354.7202 [M−H]−, 356.7268 [M+H]+.

Aufarbeitung

  1. customSolvents were then evaporated
  2. customthe residue was purified by silica column (DCM/MeOH, 39:1→19:1→9:1→4:1)

Quellen und Nachweise

ORD-Eintrag
ord-ac78428e0f6f45f586177a4cb9f04ac3
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08980926B2

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