1H-Indole-7-carboxylic acid → 1H-Indole-7-carboxylic acid (4-tert-butyl-benzyl)-[2-(2,6-dichloro-phenyl)-ethyl]-amide

HRID 855360ノート

反応式

HRID 855360 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:65]=[CH:64][C:51]([CH2:52][NH:53][CH2:54][CH2:55][C:56]2[C:61]([Cl:62])=[CH:60][CH:59]=[CH:58][C:57]=2[Cl:63])=[CH:50][CH:49]=1)([CH3:47])([CH3:46])[CH3:45]>CN(C=O)C.O>[C:44]([C:48]1[CH:65]=[CH:64][C:51]([CH2:52][N:53]([CH2:54][CH2:55][C:56]2[C:57]([Cl:63])=[CH:58][CH:59]=[CH:60][C:61]=2[Cl:62])[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)([CH3:47])([CH3:45])[CH3:46]

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 68887204(4-Tert-butyl-benzyl)-[2-(2,6-dichloro-phenyl)-ethyl]-amine

生成物 1

HCID 866030641H-Indole-7-carboxylic acid (4-tert-butyl-benzyl)-[2-(2,6-dichloro-phenyl)-ethyl]-amide

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒2 回

実験手順

To a solution of 48 mg (0.3 mmol) of 1H-indole-7-carboxylic acid and 96 mg of TBTU (0.3 mmol) in 4 ml DMF, were added 0.26 ml (1.5 mmol) of N,N-diisopropylethyl amine. After stirring for 5 min at rt, 106 mg (0.3 mmol) (4-tert-butyl-benzyl)-[2-(2,6-dichloro-phenyl)-ethyl]-amine in 1 ml DMF was added. After stirring for 2 h at rt, the reaction mixture was diluted with 50 ml water and extracted with 2×50 ml EtOAc. The combined organic phases were washed with water and brine, dried with magnesium sulfate, filtered and concentrated in vacuo. The residue was crystallized from diethylether, leading to 123 mg white solid (85%). MS (ISP) 479.5 (M+H)+.

後処理

  1. stirringAfter stirring for 2 h at rt
  2. extractionextracted with 2×50 ml EtOAc
  3. washThe combined organic phases were washed with water and brine
  4. dry with materialdried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was crystallized from diethylether

出典と根拠

ORDレコード
ord-ba0587d75ad5407290e4ff2d69e22adb
出典データセット
uspto-grants-2007_08
特許番号
US07259183B2

反応ノート

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