Molecules 2019, 24, 1594
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5.0 Hz, 2H, Ar-3,5H), 7.67 (brs, 2H, Ar-2, 6H), 7.43 (s, 1H, Pyrrole-3H), 5.65 (s, 2H, NCH2O), 3.78 (s,
3H, CH3), 3.51 (t, J = 7.5 Hz, 2H, OCH2CH2Si), 0.82 (t, J = 7.5 Hz, 2H, OCH2CH2Si), 0.08 (s, 9H,
Si(CH3)3). 13C-NMR (100 MHz, DMSO-d6)
: 160.9, 138.4, 128.5, 126.9, 126.1 (q, J = 3.7 Hz), 125.6, 125.1
−
δ
(q, J = 236.0 Hz), 123.2, 122.3, 116.5, 77.1, 65.7, 51.7, 17.5,
1.0. HRMS (ESI): m/z [M + H]+ calcd for
−
C19H25F3NO3Si: 400.1550; found: 400.1567.
Methyl 4-(4-methoxyphenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrole-2-carboxylate (3j). Colorless oil,
1
77% yield. H-NMR (400 MHz, DMSO-d6)
δ: 7.68 (d, J = 1.6 Hz, 1H, Pyrrole-5H), 7.53 (d, J = 8.8 Hz,
2H, Ar-2,6H), 7.25 (d, J = 2.0 Hz, 1H, Pyrrole-3H), 6.92 (d, J = 8.8 Hz, 2H, Ar-3,5H), 5.63 (s, 2H, NCH2O),
3.76 (s, 3H, CH3), 3.75 (s, 3H, CH3), 3.50 (t, J = 8.0 Hz, 2H, OCH2CH2Si), 0.81 (t, J = 8.0 Hz, 2H,
OCH2CH2Si),
−
0.07 (s, 9H, Si(CH3)3). 13C-NMR (100 MHz, DMSO-d6)
δ
: 161.0, 158.3, 126.8, 126.6,
126.4, 123.8, 122.5, 115.8, 114.6, 76.8, 65.5, 55.5, 51.5, 17.6,
C19H28NO4Si: 362.1782; found: 362.1792.
−
1.0. HRMS (ESI): m/z [M + H]+ calcd for
Methyl 4-(2-methoxyphenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrole-2-carboxylate (3k). Colorless
1
oil, 87% yield. H-NMR (400 MHz, DMSO-d6)
δ: 7.76 (d, J = 2.0 Hz, 1H, Pyrrole-5H), 7.59 (dd, J = 8.0,
2.0 Hz, 1H, Ar-6H), 7.37 (d, J = 2.0 Hz, 1H, Pyrrole-3H), 7.20 (td, J = 7.6, 1.6 Hz, 1H, Ar-4H), 7.05 (d, J =
7.6 Hz, 1H, Ar-3H), 6.95 (td, J = 7.6, 1.2 Hz, 1H, Ar-5H), 5.67 (s, 2H, NCH2O), 3.86 (s, 3H, CH3), 3.77
(s, 3H, CH3), 3.51 (t, J = 7.6 Hz, 2H, OCH2CH2Si), 0.82 (t, J = 7.6 Hz, 2H, OCH2CH2Si),
Si(CH3)3). 13C-NMR (100 MHz, DMSO-d6)
: 161.1, 156.3, 129.9, 127.7, 122.6, 121.6, 121.2, 120.0, 118.0,
1.0. HRMS (ESI): m/z [M + H]+ calcd for C19H28NO4Si: 362.1782;
−
0.06 (s, 9H,
δ
112.1, 76.7, 65.4, 55.8, 51.5, 17.6,
found: 362.1784.
−
Methyl 4-(p-tolyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrole-2-carboxylate (3l). Colorless oil, 73%
1
yield. H-NMR (400 MHz, DMSO-d6)
δ: 7.74 (d, J = 2.0 Hz, 1H, Pyrrole-5H), 7.49 (d, J = 8.0 Hz, 2H,
Ar-2,6H), 7.28 (d, J = 2.0 Hz, 1H, Pyrrole-3H), 7.16 (d, J = 8.0 Hz, 2H, Ar-3,5H), 5.63 (s, 2H, NCH2O),
3.76 (s, 3H, CH3), 3.50 (t, J = 8.0 Hz, 2H, OCH2CH2Si), 2.29 (s, 3H, CH3), 0.81 (t, J = 8.0 Hz, 2H,
OCH2CH2Si),
−
0.07 (s, 9H, Si(CH3)3). 13C-NMR (100 MHz, DMSO-d6)
δ
: 161.0, 135.7, 131.4, 129.8,
127.1, 125.1, 123.9, 122.6, 116.0, 76.8, 65.5, 51.6, 21.1, 17.6,
C19H28NO3Si: 346.1833; found: 346.1839.
−
1.0. HRMS (ESI): m/z [M + H]+ calcd for
Methyl 4-(o-tolyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrole-2-carboxylate (3m). Colorless oil, 52%
1
yield. H-NMR (400 MHz, DMSO-d6)
δ
: 7.52 (d, J = 2.0 Hz, 1H, Pyrrole-5H), 7.32 (dd, J = 7.6, 2.0 Hz,
1H, Ar-6H), 7.25–7.16 (m, 3H, Ar-3,4,5H), 7.09 (d, J = 2.0 Hz, 1H, Pyrrole-3H), 5.66 (s, 2H, NCH2O), 3.76
(s, 3H, CH3), 3.51 (t, J = 8.0 Hz, 2H, OCH2CH2Si), 2.37 (s, 3H, CH3), 0.81 (t, J = 8.0 Hz, 2H, OCH2CH2Si),
−
0.07 (s, 9H, Si(CH3)3). 13C-NMR (100 MHz, DMSO-d6)
δ
: 161.0, 135.1, 134.2, 131.1, 129.5, 129.2,
127.0, 126.5, 123.4, 121.8, 119.1, 76.9, 65.5, 51.6, 21.5, 17.6,
C19H28NO3Si: 346.1833; found: 346.1843.
−
1.0. HRMS (ESI): m/z [M + H]+ calcd for
Methyl 4-(naphthalen-2-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrole-2-carboxylate (3n). Colorless
oil, 76% yield. 1H-NMR (400 MHz, DMSO-d6)
: 8.16 (dd, J = 7.2, 2.4 Hz, 1H, Ar-5H), 7.98–7.95
δ
(m, 1H, Ar-4H), 7.87 (d, J = 8.0 Hz, 1H, Ar-8H), 7.65 (d, J = 2.0 Hz, 1H, Pyrrole-5H), 7.54–7.46 (m,
4H, Ar-1,3,6,7H), 7.18 (d, J = 2.0 Hz, 1H, Pyrrole-3H), 5.73 (s, 2H, NCH2O), 3.79 (s, 3H, CH3), 3.57 (t,
J = 7.6 Hz, 2H, OCH2CH2Si), 0.84 (t, J = 7.6 Hz, 2H, OCH2CH2Si),
−
0.05 (s, 9H, Si(CH3)3). 13C-NMR
(100 MHz, DMSO-d6) : 161.0, 134.1, 132.8, 131.3, 129.9, 128.9, 127.5, 127.0, 126.7, 126.3, 126.2, 125.5,
δ
122.4, 122.2, 119.7, 77.0, 65.6, 51.7, 17.6,
382.1833; found: 382.1839.
−
1.0. HRMS (ESI): m/z [M + H]+ calcd for C22H28NO3Si:
Methyl 4-(quinolin-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrole-2-carboxylate (3o). Colorless solid,
66% yield. M.p. 52–54 ◦C. 1H-NMR (400 MHz, DMSO-d6 )
: 9.21 (d, J = 2.0 Hz, 1H, Ar-2H), 8.53
δ
(d, J = 2.0 Hz, 1H, Ar-4H), 8.06 (d, J = 2.0 Hz, 1H, Pyrrole-5H), 7.94 (d, J = 8.4 Hz, 1H, Ar-8H), 7.89
(d, J = 7.2 Hz, 1H, Ar-5H), 7.65 (td, J = 7.2, 1.6 Hz, 1H, Ar-6H), 7.57–7.53 (m, 2H, Ar-7H, Pyrrole-3H),
5.65 (s, 2H, NCH2O), 3.77 (s, 3H, CH3), 3.51 (t, J = 8.0 Hz, 2H, OCH2CH2Si), 0.80 (t, J = 8.0 Hz, 2H,
OCH2CH2Si), δ: 160.9, 149.0, 146.7, 130.1, 129.2,
0.1 (s, 9H, Si(CH3)3). 13C-NMR (100 MHz, DMSO-d6)
−