Cesium carbonate → 4-[N-[1-[N-(benzofuran-2-ylcarbonyl)amino]cyclohexanecarbonyl]amino]-1-(4-fluoro-2-trifluoromethylphenyl)piperidin-3-ol

HRID 1392385ノート

反応式

HRID 1392385 の反応式
Cl.[O:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[CH:4]=[C:3]1[C:11]([NH:13][C:14]1([C:20]([NH:22][CH:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH:24]2[OH:29])=[O:21])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)=[O:12].Br[C:31]1[CH:36]=[CH:35][C:34]([F:37])=[CH:33][C:32]=1[C:38]([F:41])([F:40])[F:39].C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.C(OCC)(=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[O:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[CH:4]=[C:3]1[C:11]([NH:13][C:14]1([C:20]([NH:22][CH:23]2[CH2:28][CH2:27][N:26]([C:31]3[CH:36]=[CH:35][C:34]([F:37])=[CH:33][C:32]=3[C:38]([F:39])([F:41])[F:40])[CH2:25][CH:24]2[OH:29])=[O:21])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)=[O:12]

参加物

7

反応物 3

HCID 10796Cesium carbonateHCID 5209832-Bromo-5-fluorobenzotrifluorideHCID 115679944-[N-[1-[N-(benzofuran-2-ylcarbonyl)amino]cyclohexanecarbonyl]amino]-3-piperidinol hydrochloride

生成物 1

HCID 693116644-[N-[1-[N-(benzofuran-2-ylcarbonyl)amino]cyclohexanecarbonyl]amino]-1-(4-fluoro-2-trifluoromethylphenyl)piperidin-3-ol

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

To the suspension of 4-[N-[1-[N-(benzofuran-2-ylcarbonyl)amino]cyclohexanecarbonyl]amino]-3-piperidinol hydrochloride (300 mg) obtained in Step 2 of Example 1 in 5 ml of toluene, were added 1-bromo-4-fluoro-2-trifluoromethylbenzene (0.198 ml), cesium carbonate (1.42 g), (S)-2,2-bis(diphenylphospino)-1,1-binaphtyl (BINAP; 45.4 mg) and tris(dibenzylideneacetone)dipalladium (1.42 g). The reaction mixture was stirred for about 4 hours at 100° C. under nitrogen atmosphere, was diluted with 30 ml of ethyl acetate, filtered, and concentrated. The resulting residue was purified with column chromatography to give 179 mg of the titled compound.

後処理

  1. filtrationfiltered
  2. concentrationconcentrated
  3. customThe resulting residue was purified with column chromatography

出典と根拠

ORDレコード
ord-28949b92e49a4da1baaf12636fa823fc
出典データセット
uspto-grants-2008_03
特許番号
US07342027B2

反応ノート

読み込み中…