, 4-Methoxyphenyl)oxazol-5-yl)benzonitrile (25): Following procedure A
, -methoxyphenyl)oxazole 13b (0.175 g, 1 mmol), product 25 was obtained in 85% yield (0.235 g) as a yellow solid: mp 175-177 °C. 1 H NMR (400 MHz, CDCl3): ? 8.04 (d, J = 8.6 Hz, 2H), vol.7
13 C NMR (100 MHz, CDCl3): ? 162.6, 161.9 ,
, -Methoxyphenyl)oxazol-2-yl)benzonitrile (26): Following procedure A, from 4-bromoanisole (0.374 g, 2 mmol) and 4-(oxazol-2-yl)benzonitrile 3b (0.170 g, 1 mmol) at 150 °C, product 26 was obtained in 86%, H, 4.28. LRMS calcd for M + C17H12N2O2 276, found 276. 4
, , vol.8
, Hz, 2H), 7.66 (d, J = 8.6 Hz, 2H), vol.7
, Hz, 2H), 3.87 (s, 3H). 13 C NMR (100 MHz
, H, 4.51. LRMS calcd for M + C17H12N2O2 276
, Following procedure A, from 4-bromofluorobenzene (0.350 g, 2 mmol) and 2-(4-methoxyphenyl)oxazole 13b (0.175 g, 1 mmol), product 27 was obtained in 77% yield
34 (s, 1H), 7.13 (t, J = 8.6 Hz, 2H), 6.99 (d, J = 8.6 Hz, 2H), 3.87 (s, 3H). 13 C NMR (100 MHz, CDCl3): ? 162.6 (d, J = 248, ? 8.03 (d, J = 8.6 Hz, 2H), 7.67 (dd, J = 8.6, 5.2 Hz, 2H), vol.7 ,
, H, 4.20. LRMS calcd for M + C16H12NO2 269
, Following procedure A, from 1-bromo-4-tertbutylbenzene (0.426 g, 2 mmol) and 2-(4-methoxyphenyl)oxazole 13b (0.175 g, 1 mmol)
, 36 (s, 1H), 7.00 (d, J = 8.6 Hz, 2H), 3.87 (s, 3H), 1.36 (s, 9H). 13 C NMR, Hz, 2H), 7.64 (d, J = 8.4 Hz, 2H), 7.46 (d, J = 8.4 Hz, 2H), vol.7
, H, 6.98. LRMS calcd for M + C20H21NO2 307, p.307
, Following procedure B, from 4-bromofluorobenzene (0.350 g, 2 mmol) and 4-(oxazol-5-yl)benzonitrile 3a (0.170 g, 1 mmol), product 29 was obtained in 79% yield, -Fluorophenyl)oxazol-5-yl)benzonitrile
, , vol.8
, Hz, 2H), 7.73 (d, J = 8.5 Hz, 2H), 7.57 (s, 1H), 7.19 (t, J = 8.6 Hz, 2H). 13 C NMR (100 MHz, CDCl3): ?
,
, LRMS calcd for M + C16H9FN2O 264
, Butyl)phenyl)oxazol-5-yl)benzonitrile (30): Following procedure B, from 1-bromo-4-tert-butylbenzene (0.426 g, 2 mmol) and 4-(oxazol-5-yl)benzonitrile 3a (0.170 g, 1 mmol), product 30 was obtained in 77% yield (0.232 g) as a yellow solid
,
,
, Hz, 2H), 1.37 (s, 9H). 13 C NMR (100 MHz, CDCl3): ?
, H, 5.82. LRMS calcd for M + C20H18N2O 302
, Hz, 2H), 7.62 (d, J = 8.2 Hz, 2H), 7.58-7.48 (m, 3H), 7.37-7.26 (m, 5H). 13 C NMR (100 MHz, CDCl3): ?
, 025 mmol) at 150 °C during 24 h in DMA (4 mL) under argon affords the coupling product 31c after evaporation of the solvent and purification on silica gel in 94% yield (0.152 g) as a white solid: mp 230-232 °C
, 400 MHz, CDCl3): ? 8.74 (t, J = 8.6 Hz, 2H), 8.62 (d, J = 7.9 Hz, 1H), 8.32 (d, J = 7.0 Hz, 3H), 7.77-7.65 (m, 4H), 7.07 (d, J = 8.7 Hz, 2H), 3.92 (s, 3H). 13 C NMR (100 MHz, CDCl3): ?
, The reaction of 5, vol.9
, the solvent and purification on silica gel in 90% yield (0.148 g) as a white solid: mp 261-263 °C
, , p.10
, The reaction of 5
, KOPiv (0.140 g, 1 mmol) in the presence of PdCl(C3H5)(dppb) (15.2 mg, 0.025 mmol) at 150 °C during 24 h in DMA (4 mL) under argon affords the coupling product 33c after evaporation of the solvent and purification on silica gel in 96% yield (0.174 g) as a white solid: mp 223-225 °C
, 400 MHz, CDCl3): ? 8.74 (t, J = 8.6 Hz, 2H), 8.62 (d, J = 7.9 Hz, 1H), 8.47 (d, J = 7.4 Hz, 2H), 8.34 (d, J = 6.7 Hz, 1H), 7.85-7.65 (m, 6H). 13 C NMR
, 123.5, 122.9, 121.0, 120.9. Anal. Calcd for C22H12F3NO, vol.363
, H, 3.20. LRMS calcd for M + C22H12F3NO 363, found 363. 4'-Methoxy-2-(oxazol-2-yl), p.374
, KOPiv (0.280 g, 2 mmol) in the presence of [Ru(pcymene)Cl2]2 (30.6 mg, 0.05 mmol) at 150 °C during 16 h in NMP (4 mL) under argon affords the coupling product 34 after evaporation of the solvent and purification on silica, -yl)benzonitrile 18b (0.170 g, 1 mmol), p.101
,
, ? 7.78 (d, J = 7.4 Hz, 1H), 7.71 (d, J = 7
, Hz, 1H), 7.67-7.61 (m, 2H), vol.7
2H), 6.85 (d, J = 8.6 Hz, 2H), 3.80 (s, 3H). 13 C NMR ,
,
, LRMS calcd for M + C17H12N2O2 276
, The reaction of 4-bromobenzonitrile (0.364 g, 2 mmol), 2-(oxazol-2-yl)benzonitrile 18b (0.170 g, 1 mmol), KOPiv (0.280 g, 2 mmol) in the presence of, vol.2
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