P. Fretwell et al. / Tetrahedron 56 (2000) 7525–7539
7533
evaporated. Column chromatography of the residue yielded
4 or 5.
and 1.39 (s, 3H, CH3); m/z (%): 250 (Mϩ, 1), 133 (100), 105
(50), and 77 (10).
4a. Obtained from aryl iodide 2a (0.377 g, 1 mmol) and
tributylstannylstyrene 1a (0.435 g, 1.1 mmol) after column
chromatography eluting with 3:7 v/v ether/petroleum ether.
The product (0.314 g, 89%) was obtained as colourless
prisms from ether/petroleum ether, mp 90–92ЊC. (Found:
C, 85.0; H, 6.6; N, 3.9. C25H23NO requires: C, 85.0; H, 6.5;
N, 3.9%); d 7.30–6.96 (m, 13H ArH), 6.62 (d, 1H, J5 Hz,
ArH), 6.40 (d, 1H, J10 Hz, CvCHPh), 5.82 (m, 1H,
CH2CHvCH), 5.17, 4.60 (2×d, 2H, J10 Hz, NCH2Ph),
2.81 (m, 2H, CH2CHvC), and 1.47 (s, 3H, CH3); m/z
(%): 353 (Mϩ, 22), 236 (61), 117 (100), and 91 (91).
5b. Obtained from aryl iodide 2b (0.276 g, 1 mmol) and
2-furyltributylstannane (0.393 g, 1.1 mmol) after column
chromatography eluting with 1:9 v/v ether/petroleum
ether. The product (0.203 g, 95%) was obtained as a colour-
less oil. (Found: C, 78.4; H, 6.7. C14H14O2 requires: C, 78.5;
H, 6.5%); d 7.31, 6.27, 5.95 (3s, 3H, ArH), 7.13 (t, 1H,
J8 Hz, ArH), 7.02 (d, 1H, J7 Hz, ArH), 6.86 (t, 1H,
J7 Hz, ArH), 6.77 (d, 1H, J8 Hz, ArH), 4.55, 4.13
(2×d, 2H, J10 Hz, OCH2), 2.91 (s, 2H, CH2CO), and
1.34 (s, 3H, CH3); m/z (%): 214 (Mϩ, 3), 133 (100), and
105 (70).
4b. Obtained from aryl iodide 2a (0.377 g, 1 mmol) and
2-furyltributylstannane 1b (0.393 g, 1.1 mmol) after column
chromatography eluting with 3:7 v/v ether/petroleum ether.
The product (0.285 g, 90%) was obtained as colourless
prisms from ether/petroleum ether, mp 89–91ЊC. (Found:
C, 79.6; H, 6.1; N, 4.5. C21H19NO2 requires: C, 79.5; H, 6.0;
N, 4.4%); d 7.26–7.09 (m, 8H, ArH), 7.00 (d, 1H, J7 Hz,
ArH), 6.60 (d, 1H, J8 Hz, ArH), 6.14, 5.80 (2×s, 2H,
ArH), 5.04 and 4.72 (2×d, 2H, J16 Hz, NCH2Ph), 3.19
(dd, 2H, J9 and 3 Hz, CH2CO), and 1.50 (s, 3H, CH3);
m/z (%): 317 (Mϩ, 30), 236 (87), and 91 (100).
5c. Obtained from aryl iodide 2b (0.276 g, 1 mmol) and
3-tributylstannylindole derivative 1c (0.600 g, 1.1 mmol)
after column chromatography eluting with 1:4 v/v ether/
petroleum ether. The product (0.346 g, 86%) was obtained
as colourless prisms from ether/petroleum ether, mp 88–
90ЊC. (Found: C, 71.5; H, 5.4; N, 3.5. C24H21NO3S requires:
C, 71.5; H, 5.2; N, 3.5%); d 7.97–6.72 (m, 14H, ArH), 4.39,
4.06 (2×d, 2H, J9 Hz, OCH2), 2.95 (s, 2H, CH2CCN), and
1.40 (s, 3H, CH3); m/z (%): 403 (Mϩ, 11), 271 (75), 133
(100), and 77 (78).
5d. Obtained from aryl iodide 2b (0.276 g, 1 mmol) and
2-tributylstannylindole SEM-derivative 1d (0.589 g,
1.1 mmol) after column chromatography eluting with 1:19
v/v ether/petroleum ether. The product (0.255 g, 65%) was
obtained as a colourless oil. (Found: C, 73.2; H, 7.8; N, 3.6.
C24H31NO2Si requires: C, 73.3; H, 7.9; N, 3.6%); d 7.64,
7.45 (2×d, 2H, J8 Hz, ArH), 7.30–6.82 (m, 6H, ArH),
6.40 (s, 1H, ArH), 5.25, 4.88 (2×d, 2H, J12 Hz,
OCH2N), 4.63, 4.31 (2×d, 2H, J9 Hz, OCH2), 3.45 (t,
2H, J8 Hz, OCH2CH2), 3.33, 3.17 (2×d, 2H, J15 Hz,
CH2CN), 1.58 (s, 3H, CH3), 0.90 (t, 2H, J8 Hz, CH2Si),
and 0.00 (s, 9H, SiMe3); m/z (%): 393 (Mϩ, 7), 261 (29), 144
(68), 133 (100), 105 (37), and 73 (50).
4c. Obtained from aryl iodide 2a (0.377 g, 1 mmol) and
3-tributylstannylindole derivative 1c (0.584 g, 1.1 mmol)
after column chromatography eluting with 2:5 v/v ether/
petroleum ether. The product (0.404 g, 80%) was obtained
as colourless prisms from ether/petroleum ether, mp 169–
171ЊC. (Found: C, 73.4; H, 5.1; N, 5.8. C31H26N2O3S
requires: C, 73.5; H, 5.1; N, 5.5%); d 7.84, 7.54 (2×d,
2H, J8 Hz, ArH), 7.43–6.39 (m, 17H, ArH), 4.86, 4.33
(2×d, 2H, J16 Hz, NCH2Ph), 3.47, 3.16 (2×d, 2H,
J14 Hz, CH2CCN), and 1.58 (s, 3H, CH3); m/z (%): 506
(Mϩ, 5), 270 (100), 141 (10), and 91 (41).
4d. Obtained from aryl iodide 2a (0.377 g, 1 mmol) and
2-tributylstannylindole SEM-derivative 1d (0.600 g,
1.1 mmol) after column chromatography eluting with 2:3
v/v ether/petroleum ether. The product (0.409 g, 82%)
was obtained as a colourless thick oil. (Found HRMS:
496.2556. C31H36N2O2Si requires: 496.2546); d 7.33 (d,
2H, J8 Hz, ArH), 7.28–6.97 (m, 8H, ArH), 6.67, 6.51
(d, 2H, J8 Hz, ArH), 5.70 (s, 1H, ArH), 5.54–5.32
(2×d, 2H, J7 Hz, NCH2O), 5.10, 4.42 (2×d, 2H,
J15 Hz, NCH2Ph), 3.54, 3.36 (2×d, 2H, J14 Hz,
CH2CN), 3.40 (m, 2H, OCH2CH2), 1.60 (s, 3H, CH3),
0.84 (m, 2H, CH2Si), and Ϫ0.09 (s, 9H, SiMe3); m/z
(%): 496 (Mϩ, 24), 379 (21), 260 (40), 144 (100), 91 (28),
and 73 (39).
5e. Obtained from aryl iodide 2b (0.276 g, 1 mmol) and
vinyltributylstannane 1e (0.316 g, 1.1 mmol) after column
chromatography eluting with 1:19 v/v ether/petroleum
ether. The product was obtained as a colourless oil (71%)
which comprised 1:1.6 mixture of 7 and 5e. [Found
(mixture) C, 82.45; H, 7.9. C12H14O requires: C, 82.7; H,
8.1%]. 5e: d 7.10 (m, 2H, ArH), 6.88 (m, 1H, ArH), 6.80 (t,
1H, J8 Hz, ArH), 5.68 (m, 1H, CvCH), 5.23(br s, 1H,
CvCH), 5.05 (d, 1H, J16 Hz, CvCH), 4.38, 4.11 (2×d,
2H, J9 Hz, OCH2), 2.34 (d, 2H, J8 Hz, CH2), and 1.32
(s, 3H, CH3); m/z (%): 174 (Mϩ, 21), 261 (29), 133 (100),
105 (85), 91 (7), and 77 (15). 7: d 7.48 (d, 1H, J8 Hz,
ArH), 7.18 (m, 1H, ArH), 7.10 (m, 1H, CvCH2), 6.98 (m,
1H, ArH), 6.83 (d, 1H, J8 Hz, ArH), 5.73 (d, 1H,
J18 Hz, CvCH), 5.24 (d, 1H, J11 Hz, CvCH), 5.09,
4.97 (2s, 2H, CvCH2), 4.43 (s, 2H, OCH2), and 1.83 (s, 3H,
CH3).
5a. Obtained from aryl iodide 2b (0.276 g, 1 mmol) and
tributylstannylstyrene 1a (0.435 g, 1.1 mmol) after column
chromatography eluting with 1:9 v/v ether/petroleum ether.
The product (0.167 g, 67%) was obtained as a colourless oil.
(Found: C, 86.4; H, 7.0. C17H16O requires: C, 86.4; H,
6.8%); d 7.31–7.11 (m, 7H, ArH), 6.89 (t, 1H, J7 Hz,
ArH), 6.80 (d, 1H, J8 Hz, ArH), 6.40 (d, 1H, J16 Hz,
CvCHPh), 6.12 (m, 1H, CH2CHvCH), 4.43, 4.15 (2×d,
2H, J9 Hz, OCH2), 2.50 (d, 2H, J7.5 Hz, CH2CHvC),
5f. Obtained from aryl iodide 2b (0.276 g, 1 mmol) and
2-pyridyltributylstannane 1f (0.400 g, 1.1 mmol) after
column chromatography eluting with 2:3 v/v ether/petro-
leum ether. The product (0.134 g, 60%) was obtained as a
pale yellow oil. The hydrochloride salt was prepared from