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5-((Z)-2-(4-fluorophenyl)prop-1-enyl)-2,3,4,5-tetrahydro-2,8-dimethyl-1H-pyrido[4,3-b]indole → 5-(2-(4-fluorophenyl)propyl)-2,3,4,5-tetrahydro-2,8-dimethyl-1H-pyrido[4,3-b]indole

HRID 574576
ノート
印刷プレビュー

反応式

HRID 574576 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5](/[C:8](/[CH3:25])=[CH:9]\[N:10]2[C:18]3[CH:17]=[CH:16][C:15]([CH3:19])=[CH:14][C:13]=3[C:12]3[CH2:20][N:21]([CH3:24])[CH2:22][CH2:23][C:11]2=3)=[CH:4][CH:3]=1.FC1C=CC(C(=C)CN2C3C=CC(C)=CC=3C3CN(C)CCC2=3)=CC=1>CO.C(O)(=O)C.[Pd]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH3:25])[CH2:9][N:10]2[C:18]3[CH:17]=[CH:16][C:15]([CH3:19])=[CH:14][C:13]=3[C:12]3[CH2:20][N:21]([CH3:24])[CH2:22][CH2:23][C:11]2=3)=[CH:6][CH:7]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 461995815-((Z)-2-(4-fluorophenyl)prop-1-enyl)-2,3,4,5-tetrahydro-2,8-dimethyl-1H-pyrido[4,3-b]indoleHCID 594548975-(2-(4-fluorophenyl)allyl)-2,3,4,5-tetrahydro-2,8-dimethyl-1H-pyrido[4,3-b]indole

生成物 1

HCID 578759635-(2-(4-fluorophenyl)propyl)-2,3,4,5-tetrahydro-2,8-dimethyl-1H-pyrido[4,3-b]indole

試薬・触媒・溶媒 2

HCID 23938Palladium触媒
HCID 10129899
Acetic acid methanol
溶媒

実験手順

A mixture of compound 5-((Z)-2-(4-fluorophenyl)prop-1-enyl)-2,3,4,5-tetrahydro-2,8-dimethyl-1H-pyrido[4,3-b]indole and 5-(2-(4-fluorophenyl)allyl)-2,3,4,5-tetrahydro-2,8-dimethyl-1H-pyrido[4,3-b]indole (of ratio 1:3, 1.8 g, 5.38 mmol, 1 equiv) were shaken in a 250 ml Parr Shaker vessel with 180 mg of Pd/C in 50 ml of Methanol/acetic acid (10:1) mixture for 18 hours under 60 psi H2. It was filtered over a celite bed with methanol and evaporated under vacuum. The residue was diluted with ethyl acetate (500 ml) and washed with 50 ml of satd. sodium bicarbonate solution and then brine. The organic part was concentrated under reduced pressure and column purified over 100-200 silica gel using 0 to 50% ethyl acetate in hexanes as eluant, at an interval of 5%. Yield: 685 mg (38%).

後処理

  1. filtrationIt was filtered over a celite bed with methanol
  2. customevaporated under vacuum
  3. additionThe residue was diluted with ethyl acetate (500 ml)
  4. washwashed with 50 ml of satd
  5. concentrationThe organic part was concentrated under reduced pressure and column
  6. custompurified over 100-200 silica gel using 0 to 50% ethyl acetate in hexanes as eluant, at an interval of 5%

出典と根拠

ORDレコード
ord-a25546073a1548d182728256ca9c0ab8
出典データセット
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09034880B2

反応ノート

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