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11
Reaction of o-chloroaniline
with phenylacetaldehyde (1.0 equiv or 3.0 equiv) gave the expected
indole in 55 and 70% yield, respectively. Reaction of 2-chloro-5-methoxyaniline with
methyl (S)-2-N,N-di-tert-butoxycarbonyl-5-oxo-pentanoate
(1.0 equiv or 3.0 equiv) gave the 6-methoxy-tryptophan derivative
in 21 and 25% yield, respectively. Reaction of 2-chloro-5-methylaniline
with phenylacet-aldehyde (1.0 equiv or 3.0 equiv) gave the 5-methyl-3-phenyl-1H-indole in 56 and 67% yield,
respectively.
¹H NMR (300 MHz, CDCl3): δ = 8.08
(br s, 1 H), 7.77 (s, 1 H), 7.70 (dd, J = 1.2,
7.4 Hz, 2 H), 7.49 (t, J = 7.4
Hz, 2 H), 7.35-7.31 (m, 3 H), 7.10 (d, J = 8.4
Hz, 1 H), 2.52 (s, 3 H). ¹³C NMR (75
MHz, CDCl3): δ = 135.7,
134.9, 129.6, 128.7, 127.5, 125.9, 125.8, 124.0, 121.9, 119.4, 117.8,
111.0, 21.6.
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