Triphenylphosphine → HCID 69097659、化合物

HRID 518265ノート

反応式

HRID 518265 の反応式
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[Cl:12])[CH:5]=[C:4]([C@@H:13]([NH:15][C:16](=[O:32])[O:17][CH2:18][CH:19]2[C:31]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C:25]3[C:20]2=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH3:14])[N:3]=1.[CH2:33]([Sn](CCCC)(CCCC)C=C)[CH2:34]CC.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1COCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[Cl:12][C:10]1[CH:9]=[CH:8][CH:7]=[C:6]2[C:11]=1[C:2]([CH:33]=[CH2:34])=[N:3][C:4]([C@@H:13]([NH:15][C:16](=[O:32])[O:17][CH2:18][CH:19]1[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:25]=3[C:26]3[C:31]1=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH3:14])=[CH:5]2

参加物

6

反応物 3

HCID 11776TriphenylphosphineHCID 81998TributylvinyltinHCID 86665027(S)-(9H-fluoren-9-yl)methyl 1-(1,8-dichloroisoquinolin-3-yl)ethylcarbamate

生成物 1

HCID 69097659HCID 69097659、化合物

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of (S)-(9H-fluoren-9-yl)methyl-1-(1,8-dichloroisoquinolin-3-yl)ethylcarbamate (346) (36 g, 77.7 mmol, 1.0 eq) in THF (300 mL) under argon, tributyl(vinyl)stannane (27 g, 85.5 mmol, 1.1 eq), Pd(OAc)2 (5.23 g, 23.3 mmol, 0.3 eq) and PPh3 (12.2 g, 46.6 mmol, 0.6 eq) were added, and the resulting mixture was stirred at reflux for 16 h. The mixture was allowed to cool to RT and then concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (2-30% ethyl acetate-petroleum ether) to afford (S)-(9H-fluoren-9-yl)methyl 1-(8-chloro-1-vinylisoquinolin-3-yl)ethylcarbamate (347).

後処理

  1. temperatureat reflux for 16 h
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by flash column chromatography on silica gel (2-30% ethyl acetate-petroleum ether)

出典と根拠

ORDレコード
ord-ac445461c46d4a2e9b999cb45f898ac3
出典データセット
uspto-grants-2015_08
特許番号
US09115141B2

反応ノート

読み込み中…