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

HRID 1445890

반응식

HRID 1445890 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

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%.

후처리

  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)

출처 및 근거

ORD 기록
ord-b67f5df1629e4f6887454f4c59b9e5e0
출처 데이터셋
uspto-grants-2010_02
특허 번호
US07666898B2

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