18-Crown-6 → (E)-tert-butyl 2-(5-(3-(3,5-dichloro-4-fluorophenyl)-4,4,4-trifluorobut-1-enyl)-1H-indol-1-yl)-2-oxoethylcarbamate

HRID 1503705ノート

反応式

HRID 1503705 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]([C:22]([F:25])([F:24])[F:23])/[CH:11]=[CH:12]/[C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[NH:18][CH:17]=[CH:16]3)[CH:5]=[C:6]([Cl:9])[C:7]=1[F:8].[C:26]([O:30][C:31]([NH:33][CH2:34][C:35](OC1C=CC([N+]([O-])=O)=CC=1)=[O:36])=[O:32])([CH3:29])([CH3:28])[CH3:27].[F-].[K+].C1OCCOCCOCCOCCOCCOC1.CCN(C(C)C)C(C)C>C(#N)C.C(Cl)Cl>[Cl:9][C:6]1[CH:5]=[C:4]([CH:10]([C:22]([F:24])([F:23])[F:25])/[CH:11]=[CH:12]/[C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[N:18]([C:35](=[O:36])[CH2:34][NH:33][C:31](=[O:32])[O:30][C:26]([CH3:27])([CH3:28])[CH3:29])[CH:17]=[CH:16]3)[CH:3]=[C:2]([Cl:1])[C:7]=1[F:8]

参加物

8

反応物 5

HCID 2855718-Crown-6HCID 77217Boc-Gly-ONpHCID 81531DiisopropylethylamineHCID 522689Potassium FluorideHCID 86675169(E)-5-(3-(3,5-dichloro-4-fluorophenyl)-4,4,4-trifluorobut-1-en-1-yl)-1H-indole

生成物 1

HCID 86675171(E)-tert-butyl 2-(5-(3-(3,5-dichloro-4-fluorophenyl)-4,4,4-trifluorobut-1-enyl)-1H-indol-1-yl)-2-oxoethylcarbamate

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 6344Dichloromethane溶媒

実験手順

To a stirred solution of (E)-5-(3-(3,5-dichloro-4-fluorophenyl)-4,4,4-trifluorobut-1-enyl)-1H-indole (0.1 g, 0.258 mmol) in acetonitrile (5.0 mL) was added 4-nitrophenyl 2-(tert-butoxycarbonylamino)acetate (0.114 g, 0.387 mmol), potassium fluoride (0.03 g, 0.516 mmol), 18-crown-6-ether (0.075 g, 0.283 mmol) and DIEA (0.0332 g, 0.258 mmol) and the reaction was stirred at RT for 16 h. The reaction mixture was concentrated to obtain a residue which was diluted with DCM and washed with water and brine solution. The separated DCM layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford the crude title compound as a light brown gummy material which was used in the next step without further purification (0.1 g): ESIMS m/z 545.23 ([M+H]+).

後処理

  1. concentrationThe reaction mixture was concentrated
  2. customto obtain a residue which
  3. washwashed with water and brine solution
  4. dry with materialThe separated DCM layer was dried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-368eb2b852674a5ea7ff0d120ce86ef6
出典データセット
uspto-grants-2015_12
特許番号
US09212164B2

反応ノート

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