4-(Trifluoromethoxy)phenylboronic acid → HCID 22032973, compound

HRID 2221245Notes

Reaction equation

HRID 2221245 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]([CH3:18])=[CH:14][CH:13]=1)[CH:6]=[CH:5]2.[F:19][C:20]([F:32])([F:31])[O:21][C:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][CH:23]=1>>[CH3:18][C:15]1[CH:16]=[CH:17][C:12]([CH2:11][N:7]2[C:8]3[C:4](=[CH:3][C:2]([C:25]4[CH:24]=[CH:23][C:22]([O:21][C:20]([F:19])([F:31])[F:32])=[CH:27][CH:26]=4)=[CH:10][CH:9]=3)[CH:5]=[CH:6]2)=[CH:13][CH:14]=1

Participants

3

Reactant 2

HCID 27343864-(Trifluoromethoxy)phenylboronic acidHCID 3619668HCID 3619668, compound

Product 1

HCID 22032973HCID 22032973, compound

Procedure

The title compound was prepared from 5-bromo-1-(4-methylbenzyl)-1H-indole (Step 1 of Example 25) and 4-(trifluoromethoxy)phenylboronic acid in substantially the same manner, as described in Step 2 of Example 25. The product was obtained as an oil. Mass spectrum (ESI, [M+H]+) m/z 382. 1HNMR (300 MHz, DMSO-d6): δ 7.83 (s, 1H), 7.76 (d, 2H, J=8.8 Hz), 7.52 (s, 1H), 7.53 (d, 2H, J=8.1 Hz), 7.41-7.38 (m, 3H), 7.11 (m, 4H), 6.54 (d, 1H, J=3 Hz), 5.39 (s, 2H), and 2.23 ppm (s, 3H). Elemental Analysis for C23H18F3NO: Calculated: C, 72.43; H, 4.76; N, 3.67. Found: C, 72.38; H, 4.70; N, 3.59.

Workup

  1. customThe product was obtained as an oil

Sources & evidence

ORD record
ord-b6bfac2845e74107bdd6f356ffcb6abe
Source dataset
uspto-grants-2008_05
Patent number
US07368471B2

Reaction notes

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