Binap, (A+-)- → 2-[3-(Oxazol-5-yl)phenylamino]-6-(3-acetamidophenyl)pyrazine

HRID 16261Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 16261
[C:1]([NH:4][C:5]1[CH:6]=[C:7]([C:11]2[CH:16]=[N:15][CH:14]=[C:13](Cl)[N:12]=2)[CH:8]=[CH:9][CH:10]=1)(=[O:3])[CH3:2].[O:18]1[C:22]([C:23]2[CH:24]=[C:25]([CH:27]=[CH:28][CH:29]=2)[NH2:26])=[CH:21][N:20]=[CH:19]1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1>[O:18]1[C:22]([C:23]2[CH:24]=[C:25]([NH:26][C:13]3[N:12]=[C:11]([C:7]4[CH:6]=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[CH:10]=[CH:9][CH:8]=4)[CH:16]=[N:15][CH:14]=3)[CH:27]=[CH:28][CH:29]=2)=[CH:21][N:20]=[CH:19]1

Komponenten

6

Edukt 4

HCID 634876Binap, (A+-)-HCID 27392893-(1,3-Oxazol-5-yl)anilineHCID 116874302-(3-Acetamidophenyl)-6-chloropyrazineHCID 23676156Sodium t-butoxide

Produkt 1

HCID 115742732-[3-(Oxazol-5-yl)phenylamino]-6-(3-acetamidophenyl)pyrazineAusbeute 25,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

Using Method L, 2-(3-acetamidophenyl)-6-chloropyrazine (4a) (60 mg, 0.24 mmol), 3-(1,3-oxazol-5-yl)aniline (56.1 mg, 0.35 mmol), Pd(0)2 dba3 (9 mg, 0.01 mmol), BINAP (50 mg, 0.04 mmol), sodium tert-butoxide (33 mg, 0.34 mmol) and toluene (5 mL) were reacted at 85° C. for 16 hours. The same workup as for Method L and a combination of column chromatography and preparative TLC afforded 23 mg of pure title compound. Yield: 25.8%. 1H NMR (250 MHz, DMSO-d6) δ 2.08 (s, 3H), 7.36 (d, 1H, 8.0 Hz), 7.48 (t, 2H, 8.3 Hz), 7.61 (s, 1 H), 7.65 (d, 1 H, 8.4 Hz), 7.82 (d, 2 H, 7.3 Hz), 8.23 (s, 1 H), 8.39 (bs, 2 H), 8.46 (s, 1 H), 8.47 (s, 1 H), 9.82 (s, 1 H), 10.09 (s, 1 H); 13C NMR (62.9 MHZ, DMSO-d6) δ 24.0, 113.4, 117.1, 117.3, 118.3, 120.3, 121.3, 121.8, 127.9, 129.3, 129.8, 130.3, 133.7, 137.0, 139.9, 141.4, 147.9, 150.8, 151.3, 151.7, 168.5; m/z 372.2 [(M+H)+, calcd for C21H17N5O2 371.1].

Aufarbeitung

  1. customwere reacted at 85° C. for 16 hours

Quellen und Nachweise

ORD-Eintrag
ord-8fe4e11a0b2e40afa2ec35c2330aa193
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737152B2

Notizen zur Reaktion

Wird geladen…