4-(Trifluoromethoxy)phenylboronic acid → Ethyl 1-benzyl-5-[4-(trifluoromethoxy)phenyl]-1H-indole-2-carboxylate

HRID 2373475Notes

Reaction equation

HRID 2373475 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][CH:15]=[CH:14][CH:13]=1)[C:6]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:5]2.[F:23][C:24]([F:36])([F:35])[O:25][C:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1>>[CH2:11]([N:7]1[C:8]2[C:4](=[CH:3][C:2]([C:29]3[CH:28]=[CH:27][C:26]([O:25][C:24]([F:23])([F:35])[F:36])=[CH:31][CH:30]=3)=[CH:10][CH:9]=2)[CH:5]=[C:6]1[C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

3

Reactant 2

HCID 27343864-(Trifluoromethoxy)phenylboronic acidHCID 21964289Ethyl 1-benzyl-5-bromo-1H-indole-2-carboxylate

Product 1

HCID 21964294Ethyl 1-benzyl-5-[4-(trifluoromethoxy)phenyl]-1H-indole-2-carboxylate

Procedure

The title compound was prepared from ethyl 5-bromo-1-benzyl-1H-indole-2-carboxylate and 4-(trifluoromethoxy)phenylboronic acid in substantially the same manner, as described in step 2 of Example 1. The product was obtained as an oil. Mass spectrum (ESI, [M+H]+) m/z 440. 1H NMR (400 MHz, DMSO-d6) δ 8.01 (s, 1H), 7.79 (d, 2H, J=8.86 Hz), 7.67 (d, 1H, J=8.85 Hz), 7.62 (dd, 1H, J=8.70 and 1.68 Hz), 7.44-7.42 (m, 2H), 7.28-7.20 (m, 3H), 7.04 (d, 2H, J=7.94 Hz), 5.88 (s, 2H), 4.28 (q, 2H), 1.29 (t, 3H).

Workup

  1. customThe product was obtained as an oil

Sources & evidence

ORD record
ord-039d730ce0ab4175ba585b10f96dda24
Source dataset
uspto-grants-2008_12
Patent number
US07459478B2

Reaction notes

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