2-Methylphenyl boronic acid → HCID 22032941, compound

HRID 2221266Notes

Reaction equation

HRID 2221266 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:14][CH:13]=1)[CH:6]=[CH:5]2.[CH3:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1B(O)O>>[C:18]([C:15]1[CH:16]=[CH:17][C:12]([CH2:11][N:7]2[C:8]3[C:4](=[CH:3][C:2]([C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=4[CH3:22])=[CH:10][CH:9]=3)[CH:5]=[CH:6]2)=[CH:13][CH:14]=1)([CH3:20])([CH3:21])[CH3:19]

Participants

3

Reactant 2

HCID 27332672-Methylphenyl boronic acidHCID 21964287HCID 21964287, compound

Product 1

HCID 22032941HCID 22032941, compound

Procedure

The title compound was prepared from 5-bromo-1-[4-(tert-butyl)benzyl]-1H-indole (Step 1 of Example 34) and 2-methylphenylboronic acid in substantially the same manner, as described in Step 2 of Example 25. The product was obtained as a brown oil. Mass spectrum (ESI, [M+H]+) m/z 354. 1HNMR (400 MHz, DMSO-d6): δ 7.53 (d, 1H, J=3.06 Hz), 7.50 (d, 1H, J=8.55 Hz), 7.46 (d, 1H, J=0.95 Hz), 7.33 (d, 2H, J=7.96 Hz), 7.26-7.18 (m, 5H), 7.05 (d, 1H, J=8.40 Hz), 6.48 (d, 1H, J=3.06 Hz), 5.38 (s, 2H), 2.22 (s, 3H), and 1.22 ppm (s, 9H). Elemental Analysis for C26H27N: Calculated: C, 88.34; H, 7.70; N, 3.96. Found: C, 88.28; H, 7.58; N, 3.75.

Workup

  1. customThe product was obtained as a brown oil

Sources & evidence

ORD record
ord-a8ade4737e894ba3bcc03428f67fb54c
Source dataset
uspto-grants-2008_05
Patent number
US07368471B2

Reaction notes

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