Acetonitrile → HCID 136337207, Verbindung

Reaktionsgleichung

C([C:3]1[C:7]([C:8]([OH:10])=[O:9])=[C:6]([NH2:11])[N:5]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14](Cl)[N:13]=2)[N:4]=1)C.[OH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].[C:35](#N)[CH3:36]>>[NH2:11][C:6]1[N:5]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[OH:19])[N:13]=2)[N:4]=[CH:3][C:7]=1[C:8]([O:10][CH2:35][CH3:36])=[O:9]

Komponenten

Edukt 4

HCID 6342Acetonitrile

HCID 10340Sodium Carbonate

HCID 2773454(2-Hydroxyphenyl)boronic acid

HCID 86644573HCID 86644573, Verbindung

Produkt 1

HCID 136337207HCID 136337207, Verbindung

Reaktionsbedingungen

Temperatur: 85 °C

Versuchsvorschrift

To a vial containing the title compound from Example 10 Step A (200 mg, 0.75 mmol) were added 2-hydroxyphenylboronic acid (125 g, 0.90 mmol) and trans-dichlorobis(triphenylphosphine) palladium (II) (53 mg, 0.075 mmol). Acetonitrile (4 mL) and sodium carbonate (1.9 mL, 1.0 M aqueous, 1.9 mmol) were added, and the resulting mixture was degassed via nitrogen sparge. The reaction vial was capped and the reaction mixture was stirred at 85° C. After 18 h, the reaction mixture was allowed to cool to room temperature and was poured into water. The mixture was extracted with EtOAc, and the organic phase was concentrated in vacuo. Purification by chromatography on silica gel (0 to 75% EtOAc in hexanes, then 75 to 100% EtOAc) provided the title compound: LCMS m/z 324.9 [M+H]+; 1H NMR (500 MHz, CDCl3) δ 10.69 (s, 1H), 8.02 (t, J=8.0 Hz, 1H), 7.85 (dd, J=8.0, 3.5 Hz, 1H), 7.83 (s, 1H), 7.72-7.68 (m, 2H), 7.39-7.35 (m, 1H), 7.07-7.05 (m, 1H), 7.02-6.99 (m, 1H), 6.63 (br s, 2H), 4.32 (q, J=7.0 Hz, 2H), 1.37 (t, J=7.0 Hz, 3H).