Sodium hydride → 2-[1-(12-Bromo-dodecyl)-2-methyl-1H-indol-4-yloxy]-3-methylbutyric acid ethyl ester

HRID 1445890

反応式

HRID 1445890 の反応式
[H-].[Na+].[CH2:3]([O:5][C:6](=[O:22])[CH:7]([O:11][C:12]1[CH:20]=[CH:19][CH:18]=[C:17]2[C:13]=1[CH:14]=[C:15]([CH3:21])[NH:16]2)[CH:8]([CH3:10])[CH3:9])[CH3:4].[Br:23][CH:24](Br)[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]>CN(C=O)C.C(OCC)(=O)C>[CH2:3]([O:5][C:6](=[O:22])[CH:7]([O:11][C:12]1[CH:20]=[CH:19][CH:18]=[C:17]2[C:13]=1[CH:14]=[C:15]([CH3:21])[N:16]2[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][Br:23])[CH:8]([CH3:9])[CH3:10])[CH3:4]

参加物

6

反応物 3

HCID 24758Sodium hydrideHCID 113249061,1-DibromododecaneHCID 591703963-Methyl-2-(2-methyl-1H-indol-4-yloxy)-butyric acid ethyl ester

生成物 1

HCID 685477452-[1-(12-Bromo-dodecyl)-2-methyl-1H-indol-4-yloxy]-3-methylbutyric acid ethyl ester

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a mixture of NaH (60% in mineral oil, 0.42 g, 10 mmole) in anhydrous DMF (20 mL), 3-methyl-2-(2-methyl-1H-indol-4-yloxy)-butyric acid ethyl ester (2) (1.88 g, 7.0 mmole) and dibromododecane (2.30 g, 7.0 mmole) were added. The mixture was stirred at room temperature for 18 h. The reaction was diluted with ethyl acetate (50 mL) and washed with water (3×30 mL). The organic layer was separated, dried over sodium sulphate and concentrated. The residue was purified by column chromatography (10:1 Hex:EtOAc) to afford intermediate (3) Yield: intermediate (3) 1.32 g, 35%, by-product (4) 1.56 g, 31%.

後処理

  1. additionwere added
  2. washwashed with water (3×30 mL)
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography (10:1 Hex:EtOAc)

出典と根拠

ORDレコード
ord-b67f5df1629e4f6887454f4c59b9e5e0
出典データセット
uspto-grants-2010_02
特許番号
US07666898B2

関連ノート

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