Triethylamine → Ethyl 6-((3-bromophenyl)amino)-5-cyclopropyl-2-(4-fluorophenyl)benzofuran-3-carboxylate

HRID 1424873Notes

Reaction equation

HRID 1424873 reaction equation
[NH2:1][C:2]1[C:22]([CH:23]2[CH2:25][CH2:24]2)=[CH:21][C:5]2[C:6]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:7]([C:9]3[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=3)[O:8][C:4]=2[CH:3]=1.[Br:26][C:27]1[CH:28]=[C:29](B(O)O)[CH:30]=[CH:31][CH:32]=1.C(N(CC)CC)C>CCOC(C)=O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[Br:26][C:27]1[CH:32]=[C:31]([NH:1][C:2]2[C:22]([CH:23]3[CH2:25][CH2:24]3)=[CH:21][C:5]3[C:6]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:7]([C:9]4[CH:10]=[CH:11][C:12]([F:15])=[CH:13][CH:14]=4)[O:8][C:4]=3[CH:3]=2)[CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 2734318(3-Bromophenyl)boronic acidHCID 67353798Ethyl 6-amino-5-cyclopropyl-2-(4-fluorophenyl)benzofuran-3-carboxylate

Product 1

HCID 71258359Ethyl 6-((3-bromophenyl)amino)-5-cyclopropyl-2-(4-fluorophenyl)benzofuran-3-carboxylateYield 51%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of ethyl 6-amino-5-cyclopropyl-2-(4-fluorophenyl)benzofuran-3-carboxylate (1.00 g, 2.95 mmol), (3-bromophenyl)boronic acid (1.184 g, 5.89 mmol), copper(II) acetate (0.803 g, 4.42 mmol), triethylamine (1.232 mL, 8.84 mmol) and 4 A molecular sieves (2 g) was stirred at room temperature for 24 hours. The reaction mixture was diluted with EtOAc and filtered through Celite. The solvent was evaporated and the residue was purified by chromatography on silica gel (hexane:EtOAc) to give ethyl 6-((3-bromophenyl)amino)-5-cyclopropyl-2-(4-fluorophenyl)benzofuran-3-carboxylate (740 mg, 51%). LCMS (m/z, ES+)=494, 496 (M+H, M+2).

Workup

  1. filtrationfiltered through Celite
  2. customThe solvent was evaporated
  3. customthe residue was purified by chromatography on silica gel (hexane:EtOAc)

Sources & evidence

ORD record
ord-0799e9806efe4e27b1c8eb66b6931d94
Source dataset
uspto-grants-2015_01
Patent number
US08927593B2

Reaction notes

Loading…