ACCEPTED MANUSCRIPT
mmol), Cs2CO3 (90 mg, 0.275 mmol), [Cp*IrCl2]2 (5 mg, 0.00625 mmol) and the appropriate N-protected ethanolamine
2a-c, 4a-e or 7a-b (0.75 mmol) was stirred under N2 atmosphere at 150 °C for 48 h in a sealed vial. After cooling to
room temperature the reaction mixture was dissolved in EtOAc/MeOH 9:1 (1 mL) and filtered through a silica gel pad.
The filtrate was concentrated in vacuo and the residue was purified by flash column chromatography on silica gel.
N-(3-(1H-Indol-3-yl)propyl)acetamide (3a). Prepared according to the general procedure from 1H-indole and N-(3-
hydroxypropyl)acetamide 2a. Flash chromatography (EtOAc) gave 3a (29 mg, 54%) as a light oil. MS (ESI): 217
[M+H]+. 1H NMR (400 MHz, CDCl3): δ 1.88-1.98 (m, 2H), 1.92 (s, 3H), 2.80 (t, 2H, J=7.5 Hz), 3.31 (dt, 2H, J1 ≈ J2 =
7.5 Hz), 5.62 (brs, 1H), 6.70 (d, 1H, J = 1.5 Hz), 7.12 (ddd, 1H, J1 = 1.0, J2 = 7.0, J3 = 8.0 Hz), 7.20 (ddd, 1H, J1 = 1.0,
J2 = 7.0, J3 = 8.0 Hz), 7.36 (dd, 1H, J = 8.0 Hz), 7.59 (dd, 1H, J = 8.0 Hz), 8.26 (brs, 1H). 13C NMR (100 MHz, CDCl3):
δ 22.6, 23.3, 29.7, 39.5, 111.2, 115.3, 118.7, 119.1, 121.6, 121.9, 127.3, 136.4, 170.3. The chemical-physical data are
according to those published the literature.20
N-(4-(1H-Indol-3-yl)butyl)acetamide (3b). Prepared according to the general procedure from 1H-indole and N-(4-
hydroxybutyl)acetamide 2b. Flash chromatography (EtOAc) gave 3b (44 mg, 76%) as a light oil MS (ESI): 231
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[M+H]+. H NMR (400 MHz, CDCl3): δ 1.53-1.61 (m, 2H), 1.70-1.77 (m, 2H), 1.93 (s, 3H), 2.78 (t, 2H, J = 7.0 Hz),
3.23-3.28 (m, 2H), 5.57 (brs, 1H), 6.96 (d, 1H, J = 1.5 Hz ), 7.12 (ddd, 1H, J1 = 1.0, J2 = 7.0, J3 = 8.0 Hz), 7.19 (ddd,
1H, J1 = 1.0, J2 = 7.0, J3 = 8.0 Hz), 7.35 (ddd, 1H, J1 = J2 = 1.0 and J3 = 8.0 Hz), 7.59 (d, 1H, J = 8.0 Hz), 8.20 (brs, 1H).
13C NMR (100 MHz, CDCl3): δ 23.3, 24.7, 27.4, 29.3, 39.6, 111.2, 116.1, 118.8, 119.1, 121.4, 121.8, 127.4, 136.4,
170.2; FTIR (nujol, cm-1): 1626, 3285; Anal. Calcd. For C14H18N2O (230.14): C, 73.01; H, 7.88; N, 12.16; Found: C,
73.12; H, 7.85; N, 12.19.
N-(8-(1H-Indol-3-yl)octyl)acetamide (3c). Prepared according to the general procedure from 1H-indole and N-(8-
hydroxyoctyl)acetamide 2c. Flash chromatography (EtOAc) gave 3c (41 mg, 57%) as a light oil. MS (ESI): 287
[M+H]+. 1H NMR (400 MHz, CDCl3): δ 1.27-1.39 (m, 8H), 1.43-1.49 (m, 2H), 1.68-1.74 (m, 2H), 1.97 (s, 3H), 2.76 (t,
2H, J = 7.5 Hz), 3.19-3.24 (m, 2H), 5.74 (brs, 1H), 6.96 (s, 1H, J = 2.0 Hz), 7.12 (ddd, 1H, J1 = 1.0, J2 = 7.0, J3 = 8.0
Hz), 7.19 (ddd, 1H, J1 = 1.0, J2 = 7.0, J3 = 8.0 Hz), 7.35 (ddd, 1H, J1 = J2 = 1.0 and J3 = 8.0 Hz), 7.63 (d, 1H, J = 8.0 Hz),
8.31 (brs, 1H); 13C NMR (100 MHz, CDCl3): δ 23.3, 25.1, 26.9, 29.3, 29.4, 29.5, 29.6, 30.1, 39.8, 111.2, 116.8, 118.9,
119.0, 121.3, 121.7, 127.6, 136.4, 170.3; FTIR (film, cm-1): 1642, 3391; Anal. Calcd. For C18H26N2O (286.20): C,
75.48; H, 9.15; N, 9.78; Found: C, 75.66; H, 9.24; N, 9.91.
N-(1-(1H-Indol-3-yl)propan-2-yl)acetamide (5a). Prepared according to the general procedure from 1H-indole and
(S)-N-(1-hydroxypropan-2-yl)acetamide 4a. Flash chromatography (EtOAc) gave 5a (20 mg, 37%) as a light oil. MS
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(ESI): 217 [M+H]+. H NMR (400 MHz, CDCl3): δ 1.17 (d, 3H, J = 6.5 Hz), 1.92 (s, 3H), 2.95 (d, 2H, J = 6.0 Hz),
4.35-4.42 (m, 1H), 5.39 (brs, 1H), 7.04 (d, 1H, J = 2.0 Hz), 7.14 (ddd, 1H, J1 = 1.0, J2 = 7.0, J3 = 8.0 Hz), 7.21 (ddd, 1H,
J1 = 1.0, J2 = 7.0, J3 = 8.0 Hz), 7.38 (d, 1H, J = 8.0 Hz), 7.64 (d, 1H, J = 8.0 Hz), 8.20 (brs, 1H). 13C NMR (100 MHz,
CDCl3): δ 20.3, 23.5, 31.7, 45.6, 111.1, 111.9, 119.0, 119.6, 122.1, 122.7, 128.0, 136.2, 169.5; FTIR (nujol, cm-1):
1740, 3398; Anal. Calcd. For C13H16N2O (216.13): C, 72.19; H, 7.46; N, 12.95; Found: C, 72.28; H, 7.52; N, 12.90.
Methyl 2-acetamido-3-(1H-indol-3-yl)propanoate (5b). Prepared according to the general procedure from 1H-indole
and methyl 2-acetamido-3-hydroxypropanoate 4b. Flash chromatography (cyclohexane:EtOAc 4:6 to EtOAc) gave 5b
(20 mg, 15%) as a white solid. MS (ESI): 261 [M+H]+. 1H NMR (400 MHz, CDCl3): δ 1.96 (s, 3H), 3.31 (dd, 1H, J1 =
5.5, J2 = 15.0 Hz), 3.36 (dd, 1H, J1 = 5.5, J2 = 15.0 Hz), 3.71 (s, 3H), 4.97 (ddd, 1H, J1 ≈ J2 = 5.5, J3 = 8.0 Hz), 6.03 (brs,
1H), 6.98 (s, 1H), 7.13 (ddd, 1H, J1 = 1.0, J2 = 7.0, J3 = 8.0 Hz), 7.20 (ddd, 1H, J1 = 1.0, J2 = 7.0, J3 = 8.0 Hz), 7.37 (d,
1H, J = 8.0 Hz), 7.54 (d, 1H, J = 8.0 Hz), 8.29 (brs, 1H). 13C NMR (100 MHz, CDCl3): δ 23.2, 27.6, 52.3, 53.1, 110.0,
111.3, 118.5, 119.7, 122.3, 122.7, 127.7, 136.1, 169.8, 172.4. The chemical-physical data are according to those
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