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47
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29544451393
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note
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3 (0.025 mmol). The resulting mixture was refluxed and monitored by GC or TLC until the starting material was consumed. After the usual work-up, the crude product was purified by silica gel column chromatography to afford the 2-substituted indole 2a (91 mg, 95%) as a pale yellow solid.
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48
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29544436961
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note
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3CN were not effective for the reaction.
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49
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29544448738
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note
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3: 29%). Another group investigated a similar cyclization of an ethynylaniline derivative, see Ref. 3b.
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-
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50
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29544443422
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note
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4 = H), the corresponding indole product was not obtained under the present conditions.
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54
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17444379383
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55
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29544447444
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See Ref. 4.
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See Ref. 4.
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-
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56
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29544438355
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note
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3: C, 64.28; H, 4.46; N, 6.52. Found: C, 64.28; H, 4.41; N, 6.43.
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57
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6244279150
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Although the role of TMSCl is not clear at this stage, it is known that a coexistence of Lewis acid and TMSCl promotes reactivity of an addition reaction, see: E.J. Corey, and N.W. Boaz Tetrahedron Lett. 26 1985 6015
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66
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29544441482
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note
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3 for the second step, the desired amino acid precursor 4a was produced in 57% yield.
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67
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0033930017
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Selected papers for Lewis acid-promoted reaction of indole with imines, see: Y. Gong, K. Kato, and H. Kimoto Synlett 2000 1058
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Kimoto, H.3
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