Please do not adjust margins
Organic & Biomolecular Chemistry
Page 5 of 8
DOI: 10.1039/C8OB01501E
Journal Name
ARTICLE
122.0, 119.5, 119.1, 113.0, 19.9, 19.8; HRMS (m/z) [M + H]+ 1H, overlapped with the peak of chloroform), 6.41 (d, J = 7.2
calcd for C21H19N2, 299.1543, found 299.1543.
Hz, 1H) , 2.33 (s, 3H); 13C NMR (100 MHz, CDCl3): δ 137.6,
3-(3,4-Dichlorophenyl)-1-phenylimidazo[1,5-a]pyridine (1j).
1
135.3, 130.4, 130.35, 130.2, 129.0, 128.7, 128.6, 128.2, 128.1,
h; eluent: CH2Cl2/PE 70:30; yield: 185 mg, 94%; yellow solid, 126.7, 126.2, 121.3, 116.7, 116.1, 21.2; HRMS (m/z) [M + H]+
mp 168-169 ºC; 1H NMR (400 MHz, CDCl3): δ 8.20 (d, J = 7.2 Hz, calcd for C20H17N2, 285.1386, found 285.1386.
1H), 7.98 (d, J = 1.6 Hz, 1H), 7.91 (d, J = 7.6 Hz, 2H), 7.86 (d, J = 7-Fluoro-1,3-diphenylimidazo[1,5-a]pyridine (1r). 3 h; eluent:
9.6 Hz, 1H), 7.71-7.69 (m, 1H), 7.61-7.59 (m, 1H), 7.48 (t, J = EtOAc/PE 15:85; yield: 143 mg, 99%; yellow solid, mp 98-100
7.6 Hz, 2H), 7.32 (t, J = 7.6 Hz, 1H), 6.86-6.82 (m, 1H), 6.66 (t, J ºC; 1H NMR (400 MHz, CDCl3): δ 8.15 (d, J = 3.6 Hz, 1H), 7.90 (d,
= 6.8 Hz, 1H); 13C NMR (100 MHz, CDCl3): δ 135.6, 134.6, 133.4, J = 7.6 Hz, 2H), 7.83-7.80 (m, 3H), 7.55 (t, J = 7.6 Hz, 2H), 7.47
132.74, 132.69, 131.0, 130.2, 129.9, 128.8, 128.2, 127.0, 126.9, (t, J = 7.6 Hz, 3H), 7.33 (t, J = 7.6 Hz, 1H), 6.76-6.71 (m, 1H); 13C
121.4, 120.1, 119.4, 114.0; HRMS (m/z) [M + H]+ calcd for NMR (100 MHz, CDCl3): δ 154.3 (d, JC−F = 238.2 Hz), 139.0 (d,
C19H13Cl2N2, 339.0450, found 339.0454.
JC−F = 2.8 Hz), 134.5, 133.7, 129.8, 129.2, 129.1, 128.8, 128.1,
3-(Naphthalen-1-yl)-1-phenylimidazo[1,5-a]pyridine (1k). 6 h; 127.0, 126.9, 126.0, 120.3 (d, JC−F = 9.8 Hz), 112.7 (d, JC−F = 27.3
eluent: EtOAc/PE 15:85; yield: 159 mg, 99%; yellow solid, mp Hz), 107.6 (d, JC−F = 41.4 Hz); HRMS (m/z) [M + H]+ calcd for
119-120 ºC (lit.16b mp 123-124 ºC); 1H NMR (400 MHz, CDCl3): δ C19H14FN2, 289.1136, found 289.1136.
8.03-8.00 (m, 3H), 7.96-7.91 (m, 2H), 7.80 (dd, J = 8.0, 0.8 Hz, 1,3-Diphenylimidazo[5,1-a]isoquinoline (1s).
3 h; eluent:
1H), 7.75 (d, J = 8.0 Hz, 1H), 7.65-7.60 (m, 2H), 7.55-7.45 (m, EtOAc/PE 15:85; yield: 159 mg, 99%; yellow solid, mp 156-159
4H), 7.31 (t, J = 7.6 Hz, 1H), 6.84-6.80 (m, 1H), 6.50-6.47 (m, ºC; 1H NMR (400 MHz, CDCl3): δ 8.07 (d, J = 8.0 Hz, 1H), 7.99 (d,
1H); 13C NMR (100 MHz, CDCl3): δ 136.9, 135.1, 134.0, 132.0, J = 7.2 Hz, 1H), 7.82 (d, J = 7.6 Hz, 2H), 7.79 (d, J = 7.2 Hz, 2H),
131.7, 130.1, 129.0, 128.8, 128.6, 127.23, 127.20, 127.1, 126.8, 7.55-7.41 (m, 7H), 7.36 (t, J = 7.6 Hz, 1H), 7.29 (t, J = 8.0 Hz,
126.5, 126.4, 125.6, 125.5, 122.3, 119.9, 119.0, 112.9; HRMS 1H), 6.77 (d, J = 7.6 Hz, 1H); 13C NMR (100 MHz, CDCl3): δ
(m/z) [M + H]+ calcd for C23H17N2, 321.1386, found 321.1385.
140.4, 136.4, 135,6, 129.9, 129.8, 129.1, 129.0, 128.9, 128.6,
h; 128.0, 127.8, 127.7, 127.1, 126.8, 125.8, 124.1, 122.7, 120.8,
1-Phenyl-3-(pyridin-2-yl)imidazo[1,5-a]pyridine (1l).
2
eluent: EtOAc/PE 25:75; yield: 135 mg, 99%; yellow solid, mp 114.2; HRMS (m/z) [M + H]+ calcd for C23H17N2, 321.1386,
1
96-98 ºC (lit.16b mp 100-101 ºC); H NMR (400 MHz, CDCl3): δ found 321.1380.
10.01 (d, J = 7.6 Hz, 1H), 8.64 (d, J = 4.8 Hz, 1H), 8.50 (d, J = 8.0 3-Phenyl-1-(p-tolyl)imidazo[1,5-a]pyridine (1t). 2 h; eluent:
Hz, 1H), 7.97 (d, J = 8.0 Hz, 2H), 7.89 (d, J = 9.2 Hz, 1H), 7.81- EtOAc/PE 15:85; yield: 139 mg, 98%; yellow solid, mp 126-127
7.76 (m, 1H), 7.49 (t, J = 7.6 Hz, 2H), 7.32 (t, J = 7.6 Hz, 1H), ºC (lit.16b mp 123-124 ºC); 1H NMR (400 MHz, CDCl3): δ 8.21 (d,
7.21-7.18 (m, 1H), 6.94-6.90 (m, 1H), 6.75 (t, J = 7.2 Hz, 1H); 13
C
J = 7.2 Hz, 1H), 7.84-7.80 (m, 5H), 7.53 (t, J = 7.6 Hz, 2H), 7.44
NMR (100 MHz, CDCl3): δ 151.0, 148.1, 136.5, 134.9, 134.8, (t, J = 7.2 Hz, 1H), 7.28 (d, J = 7.6 Hz, 2H), 6.77-6.73 (m, 1H),
132.2, 129.2, 128.8, 127.0, 126.8, 126.4, 122.3, 121.7, 121.1, 6.54 (t, J = 6.8 Hz, 1H), 2.40 (s, 3H); 13C NMR (100 MHz, CDCl3):
118.4, 113.8; HRMS (m/z) [M + H]+ calcd for C18H14N3, δ 137.9, 136.3, 132.13, 132.07, 130.2, 129.5, 129.0, 128.8,
272.1182, found 272.1184.
128.4, 127.4, 126.8, 121.7, 119.4, 119.3, 113.2, 21.3; HRMS
h; (m/z) [M + H]+ calcd for C20H17N2, 285.1386, found 285.1385.
3-(Furan-2-yl)-1-phenylimidazo[1,5-a]pyridine (1m).
2
eluent: CH2Cl2/PE 50:50; yield: 112 mg, 86%; yellow solid, mp 1-(4-Methoxyphenyl)-3-phenylimidazo[1,5-a]pyridine (1u).16b
124-126 ºC (lit.16b mp 123-124 ºC); 1H NMR (400 MHz, CDCl3): δ 2 h; eluent: EtOAc/PE 15:85; yield: 143 mg, 95%; yellow solid,
1
8.66 (d, J = 7.2 Hz, 1H), 7.91 (d, J = 7.6 Hz, 2H), 7.83 (d, J = 9.2 mp 86-87 ºC; HNMR (400 MHz, CDCl3): δ 8.21 (d, J = 7.2 Hz,
Hz, 1H), 7.60 (m, 1H), 7.47 (t, J = 7.6 Hz, 2H), 7.31 (t, J = 7.6 Hz, 1H), 7.88-7.82 (m, 4H), 7.78 (d, J = 9.2 Hz, 1H), 7.53 (t, J = 7.6
1H), 7.10 (d, J = 2.8 Hz, 1H), 6.84-6.80 (m, 1H), 6.68 (t, J = 6.8 Hz, 2H), 7.44 (t, J = 7.2 Hz, 1H), 7.04-7.00 (m, 2H), 6.76-6.72
Hz, 1H), 6.61-6.60 (m, 1H); 13C NMR (100 MHz, CDCl3): δ 146.1, (m, 1H), 6.54 (t, J = 7.2 Hz, 1H), 3.86 (s, 3H); 13C NMR (100
142.2, 134.5, 132.3, 130.1, 128.8, 127.4, 127.0, 126.8, 123.3, MHz, CDCl3): δ 158.6, 137.8, 132.0, 130.2, 129.0, 128.8, 128.3,
120.0, 119.0, 113.9, 111.8, 108.9; HRMS (m/z) [M + H]+ calcd 128.1, 127.7, 127.1, 121.6, 119.2, 114.2, 113.2, 55.4; HRMS
for C17H13N2O, 261.1022, found 261.1026.
(m/z) [M + H]+ calcd for C20H17N2O, 301.1335, found 301.1337.
1-Phenyl-3-(trifluoromethyl)imidazo[1,5-a]pyridine (1p). 5 h; 1-(4-Fluorophenyl)-3-phenylimidazo[1,5-a]pyridine (1v). 3 h;
eluent: EtOAc/PE 15:85; yield: 80 mg, 61%; yellow solid, mp eluent: EtOAc/PE 15:85; yield: 139 mg, 96%; yellow solid, mp
1
1
89-90 ºC; H NMR (400 MHz, CDCl3): δ 8.15 (d, J = 7.2 Hz, 1H), 134-135 ºC (lit.10a mp 134.5-135 ºC); HNMR (400 MHz, CDCl3):
7.91 (d, J = 9.2 Hz, 1H), 7.86 (d, J = 7.6 Hz, 2H), 7.48 (t, J = 7.6 δ 8.24 (d, J = 7.2 Hz, 1H), 7.91-7.87 (m, 2H), 7.84-7.82 (m, 2H),
Hz, 2H), 7.35 (t, J = 7.2 Hz, 1H), 7.01-6.97 (m, 1H), 6.82 (t, J = 7.77 (d, J = 9.2 Hz, 1H), 7.54 (t, J = 7.6 Hz, 2H), 7.47-7.44 (m,
6.8 Hz, 1H); 13C NMR (100 MHz, CDCl3): δ 133.7, 132.2, 129.0, 1H), 7.18-7.14 (m, 2H), 6.81-6.77 (m, 1H), 6.59-6.56 (m, 1H);
128.9, 127.4, 127.1, 125.4, 122.3 (d, JC−F = 3.3 Hz), 121.6, 119.9 13C NMR (100 MHz, CDCl3): δ 161.8 (d, JC−F = 243.9 Hz), 138.1,
(d, JC−F = 266.7 Hz), 119.1, 115.0; HRMS (m/z) [M + H]+ calcd for 131.14, 131.12 130.1, 129.1, 128.9, 128.4, 128.3, 127.4, 121.8,
C14H10F3N2, 263.0791, found 263.0792.
119.8, 118.9, 115.7 (d, JC−F = 21.3 Hz), 113.3; HRMS (m/z) [M +
7-Methyl-1,3-diphenylimidazo[1,5-a]pyridine (1q). 3.5 h; H]+ calcd for C19H14FN2, 289.1136, found 289.1132.
eluent: EtOAc/PE 15:85; yield: 137 mg, 96%; yellow solid, mp 1-(4-Chlorophenyl)-3-phenylimidazo[1,5-a]pyridine (1w). 4.5
1
125-127 ºC; H NMR (400 MHz, CDCl3): δ 8.15 (d, J = 7.2 Hz, h; eluent: EtOAc/PE 15:85; yield: 148 mg, 97%; yellow solid,
1H), 7.99 (d, J = 8.0 Hz, 2H), 7.82 (d, J = 7.6 Hz, 2H), 7.59 (s, mp 177-179 ºC (lit.11e mp 177-179 ºC); 1H NMR (400 MHz,
1H), 7.52 (t, J = 7.6 Hz, 2H), 7.48-7.41 (m, 3H), 7.30-7.25 (m, CDCl3): δ 8.24 (d, J = 7.2 Hz, 1H), 7.89-7.86 (m, 2H), 7.83-7.78
This journal is © The Royal Society of Chemistry 20xx
J. Name., 2013, 00, 1-3 | 5
Please do not adjust margins