1,2-Dichloroethane → HCID 50919245、化合物

HRID 1851892ノート

反応式

HRID 1851892 の反応式
[Br:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([OH:18])=O)=[CH:13][CH:14]=3)[CH:9]=[CH:8]2)=[CH:4][CH:3]=1.Cl.[N+:22]([C:25]1[CH:30]=[CH:29][C:28]([C@@H:31]([NH2:33])[CH3:32])=[CH:27][CH:26]=1)([O-:24])=[O:23].CCN(C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([NH:33][C@H:31]([C:28]4[CH:27]=[CH:26][C:25]([N+:22]([O-:24])=[O:23])=[CH:30][CH:29]=4)[CH3:32])=[O:18])=[CH:13][CH:14]=3)[CH:9]=[CH:8]2)=[CH:19][CH:20]=1

参加物

8

反応物 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 16212176(1S)-1-(4-Nitrophenyl)ethan-1-amine--hydrogen chloride (1/1)HCID 63749115HCID 63749115、化合物

生成物 1

HCID 50919245HCID 50919245、化合物収率 87.1%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 1-(4-bromobenzyl)-1H-indole-5-carboxylic acid (1.03 g, 3.1 mmol, 1 equiv) in DMF (30 mL) were added the (S)-1-(4-nitrophenyl)ethanamine hydrochloride (695 mg, 3.4 mmol, 1.1 equiv), DIEA (600 μL, 3.4 mmol, 1.1 equiv), HOBt (525 mg, 3.4 mmol, 1.1 equiv) and EDC (658 mg, 3.4 mmol, 1.1 equiv). After stirring 4 h at room temperature, the mixture was diluted with AcOEt and washed with a 0.5 N HCl aqueous solution, a saturated NaHCO3 solution and brine, dried over MgSO4 and concentrated in vacuo. The crude was purified by flash chromatography (Hexane/AcOEt 1/1) to afford a yellow powder (1.3 g, 2.7 mmol, 87%). ESI-MS (m/z): 478/480 [M+H]+.

後処理

  1. washwashed with a 0.5 N HCl aqueous solution
  2. dry with materiala saturated NaHCO3 solution and brine, dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe crude was purified by flash chromatography (Hexane/AcOEt 1/1)

出典と根拠

ORDレコード
ord-13a79cfb971c46cd98f9d6ea70905d84
出典データセット
uspto-grants-2015_02
特許番号
US08957093B2

反応ノート

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