(Pyridin-4-yl)boronic acid → (2E)-N-Indol-5-yl-3-[2-(4-pyridyl)-4-(trifluoromethyl)phenyl]prop-2-enamide

HRID 730291Notes

Reaction equation

HRID 730291 reaction equation
Br[C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1/[CH:12]=[CH:13]/[C:14]([NH:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[NH:22][CH:21]=[CH:20]2)=[O:15].[N:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1>>[NH:22]1[C:23]2[C:19](=[CH:18][C:17]([NH:16][C:14](=[O:15])/[CH:13]=[CH:12]/[C:3]3[CH:4]=[CH:5][C:6]([C:8]([F:11])([F:10])[F:9])=[CH:7][C:2]=3[C:29]3[CH:30]=[CH:31][N:26]=[CH:27][CH:28]=3)=[CH:25][CH:24]=2)[CH:20]=[CH:21]1

Participants

3

Reactant 2

HCID 2734379(Pyridin-4-yl)boronic acidHCID 57807978(2E)-3-[2-Bromo-4-(trifluoromethyl)phenyl]-N-indol-5-ylprop-2-enamide

Product 1

HCID 57808061(2E)-N-Indol-5-yl-3-[2-(4-pyridyl)-4-(trifluoromethyl)phenyl]prop-2-enamide

Procedure

Analogous to the procedure used to prepare Example 100, (2E)-3-[2-bromo-4-(trifluoromethyl)phenyl]-N-indol-5-ylprop-2-enamide, Example 97, (120 mg, 0.29 mmol) and pyridine-4-boronic acid (72 mg, 0.59 mmol, Frontier Scientific) provided, after purification by silica gel chromatography (gradient: 0-60%EtOAc in hexane), the title product as a yellow solid. MP 229-234° C. MS (ESI, pos. ion) m/z: 408 (M+1).

Workup

  1. customprovided
  2. customafter purification by silica gel chromatography (gradient: 0-60%EtOAc in hexane)

Sources & evidence

ORD record
ord-b135c9a3d25d4c56b2c71ec24e2f2b59
Source dataset
uspto-grants-2009_09
Patent number
US07582657B2

Reaction notes

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