5-Bromoindole → HCID 22032975, compound

HRID 2221267Notes

Reaction equation

Br[CH2:2][CH:3]([CH2:6][CH3:7])[CH2:4][CH3:5].[Br:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[CH:12]2>>[Br:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH2:2][CH:3]([CH2:6][CH3:7])[CH2:4][CH3:5])[CH:13]=[CH:12]2

Participants

Reactant 2

HCID 249055-Bromoindole

HCID 77432Pentane, 3-(bromomethyl)-

Product 1

HCID 22032975HCID 22032975, compound

Procedure

The title compound was prepared from 1-bromo-2-ethylbutane (14.14 mL, 101 mmol) and 5-bromoindole (20 g, 101 mmol) in substantially the same manner, as described in Step 1 of Example 25. The product (17.78 g, 62%) was obtained as a colorless oil. Mass spectrum (ESI, [M+H]+) m/z 280. 1HNMR (400 MHz, DMSO-d6): δ 7.71 (d, 1H, J=1.83 Hz), 7.43-7.39 (m, 2H), 7.21 (dd, 2H, J=8.72 and 1.99 Hz), 6.41 (d, 1H, J=2.90 Hz), 4.04 (d, 2H, J=7.48 Hz), 1.76 (hep, 1 H), 1.21 (p, 4 H), and 0.82 ppm (t, 6 H). Elemental Analysis for C14H18BrN: Calculated: C, 60.01; H, 6.47; N, 5.00. Found: C, 60.20; H, 6.46; N, 4.96.

Sources & evidence

ORD record: ord-1405c8185f0c4b1899d0221542c9a5a4
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07368471B2

Reaction notes

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