Benzyl Bromide → Ethyl 1-benzyl-5-bromo-1H-indole-2-carboxylate

HRID 2221273Notes

Reaction equation

HRID 2221273 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5]2.[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:6]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5]2

Participants

3

Reactant 2

HCID 7498Benzyl BromideHCID 259091Ethyl 5-Bromoindole-2-carboxylate

Product 1

HCID 21964289Ethyl 1-benzyl-5-bromo-1H-indole-2-carboxylate

Procedure

The title compound was prepared from ethyl 5-bromo-1H-indole-2-carboxylate and benzyl bromide in substantially the same manner, as described in Step 1 of Example 25. The product was obtained as a light yellow solid. Mass spectrum (ESI, [M+H]+) m/z 358. 1HNMR (300 MHz, DMSO-d6): δ 7.94 (s, 1H), 7.55 (d, 1H, J=9.01 Hz), 7.42 (d, 1H, J=8.85 Hz), 7.34 (s, 1H), 7.30-7.21 (m, 3H), 6.99 (d, 2H, J=7.94 Hz), 5.85 (s, 2H), 4.28 (q, 2H), and 1.28 ppm (t, 3H). Elemental Analysis for C18H16BrNO2: Calculated: C, 60.35; H, 4.50; N, 3.91. Found: C, 69.19; H, 4.51; N, 3.75.

Workup

  1. customThe product was obtained as a light yellow solid

Sources & evidence

ORD record
ord-4a5431b559da4bae966892b28329369c
Source dataset
uspto-grants-2008_05
Patent number
US07368471B2

Reaction notes

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