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1H-Indole-7-carboxylic acid → 1H-Indole-7-carboxylic acid (4-tert-butyl-benzyl)-[2-(3-ethoxy-phenyl)-ethyl]-amide

HRID 855375
ノート
印刷プレビュー

反応式

HRID 855375 の反応式
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[C:10]([OH:12])=O)[CH:3]=[CH:2]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(CC)C(C)C)(C)C.[C:44]([C:48]1[CH:66]=[CH:65][C:51]([CH2:52][NH:53][CH2:54][CH2:55][C:56]2[CH:61]=[CH:60][CH:59]=[C:58]([O:62][CH2:63][CH3:64])[CH:57]=2)=[CH:50][CH:49]=1)([CH3:47])([CH3:46])[CH3:45]>CN(C=O)C.O>[C:44]([C:48]1[CH:66]=[CH:65][C:51]([CH2:52][N:53]([CH2:54][CH2:55][C:56]2[CH:61]=[CH:60][CH:59]=[C:58]([O:62][CH2:63][CH3:64])[CH:57]=2)[C:10]([C:8]2[CH:7]=[CH:6][CH:5]=[C:4]3[C:9]=2[NH:1][CH:2]=[CH:3]3)=[O:12])=[CH:50][CH:49]=1)([CH3:46])([CH3:45])[CH3:47]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 742811H-Indole-7-carboxylic acidHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 69342202(4-Tert-butyl-benzyl)-[2-(3-ethoxy-phenyl)-ethyl]-amine

生成物 1

HCID 866030791H-Indole-7-carboxylic acid (4-tert-butyl-benzyl)-[2-(3-ethoxy-phenyl)-ethyl]-amide収率 32.7%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 120 mg (0.74 mmol) of 1H-indole-7-carboxylic acid and 240 mg of TBTU (0.74 mmol) in 8 ml DMF, were added 0.64 ml (3.72 mmol) of N,N-diisopropylethyl amine. After stirring for 5 min at rt, 309 mg (0.94 mmol) of (4-tert-butyl-benzyl)-[2-(3-ethoxy-phenyl)-ethyl]-amine were added. After stirring for 4 h at rt, the reaction mixture was diluted with 80 ml water and extracted with EtOAc (2×). The combined organic phases were washed with brine, dried with magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography (40 g silica gel; EtOAc/heptane 1:4) to give 110 mg off-white foam (31%). MS (ISP) 455.7 (M+H)+.

後処理

  1. stirringAfter stirring for 4 h at rt
  2. extractionextracted with EtOAc (2×)
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography (40 g silica gel; EtOAc/heptane 1:4)

出典と根拠

ORDレコード
ord-495e4d8b97bd4b6abdd543578b1f942c
出典データセット
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07259183B2

反応ノート

読み込み中…

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