Piperidine → Ethyl 1-(3-(naphthalen-1-yloxy)propyl)-3-(piperidin-1-yl)-1h-indole-2-carboxylate

HRID 533249ノート

反応式

HRID 533249 の反応式
Br[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([CH2:11][CH2:12][CH2:13][O:14][C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=[CH:17][CH:16]=2)[C:3]=1[C:25]([O:27][CH2:28][CH3:29])=[O:26].[NH:30]1[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.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]>[C:15]1([O:14][CH2:13][CH2:12][CH2:11][N:4]2[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[C:2]([N:30]3[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]3)=[C:3]2[C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][CH:16]=1

参加物

8

反応物 4

HCID 8082PiperidineHCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 67316935Ethyl 3-bromo-1-(3-(naphthalen-1-yloxy)propyl)-1h-indole-2-carboxylate

生成物 1

HCID 67316989Ethyl 1-(3-(naphthalen-1-yloxy)propyl)-3-(piperidin-1-yl)-1h-indole-2-carboxylate

試薬・触媒・溶媒 3

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

実験手順

A mixture of EXAMPLE 31C (100 mg), piperidine (57 mg), tris(dibenzylideneacetone)dipalladium(0) (20 mg), 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (26 mg) and Cs2CO3 (216 mg) in toluene (2 mL) was heated at 100° C. for 48 hours. The mixture was diluted with ethyl acetate and was washed with water and brine. The organic phase was dried (Na2SO4) filtered, and concentrated. The concentrate was purified by flash chromatography on silica gel with 0-10% ethyl acetate/hexanes.

後処理

  1. washwas washed with water and brine
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe concentrate was purified by flash chromatography on silica gel with 0-10% ethyl acetate/hexanes

出典と根拠

ORDレコード
ord-967cbbe7d3394feaae49e0da53e88c12
出典データセット
uspto-grants-2014_10
特許番号
US08853209B2

反応ノート

読み込み中…