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

HRID 2272368ノート

反応式

HRID 2272368 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8895Cupric acetate触媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-7e9bf8f60e84413a8445b41a1bf6dc39
出典データセット
uspto-grants-2015_09
特許番号
US09119868B2

反応ノート

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