Cesium carbonate → Methyl 3-[1-(4-Chlorobenzyl)-5-(furo[3,2-b]pyridin-5-ylmethoxy) indol-2-yl]-2,2-dimethylpropanoate

HRID 1492412노트

반응식

HRID 1492412 반응식
[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([OH:16])=[CH:13][CH:14]=3)[CH:9]=[C:8]2[CH2:17][C:18]([CH3:24])([CH3:23])[C:19]([O:21][CH3:22])=[O:20])=[CH:4][CH:3]=1.Br[CH2:28][C:29]1[N:34]=[C:33]2[CH:35]=[CH:36][O:37][C:32]2=[CH:31][CH:30]=1.C([O-])([O-])=O.[Cs+].[Cs+]>C(#N)C>[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH2:28][C:29]4[N:34]=[C:33]5[CH:35]=[CH:36][O:37][C:32]5=[CH:31][CH:30]=4)=[CH:13][CH:14]=3)[CH:9]=[C:8]2[CH2:17][C:18]([CH3:24])([CH3:23])[C:19]([O:21][CH3:22])=[O:20])=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 14980565Methyl 3-[N-(p-chlorobenzyl)-5-hydroxyindol-2-yl]-2,2-dimethylpropanoateHCID 189505795-(Bromomethyl)furo[3,2-b]pyridine

생성물 1

HCID 23202372Methyl 3-[1-(4-Chlorobenzyl)-5-(furo[3,2-b]pyridin-5-ylmethoxy) indol-2-yl]-2,2-dimethylpropanoate

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A solution of 440 mg(1.18 mmol) of methyl 3-[1-(4-chlorobenzyl) -5-hydroxyindol-2-yl]-2,2-dimethylpropanoate, 5(bromomethyl)furo[3,2-b]pyridine (274 mg (1.3 mmol) from Step 3), and 772 mg (2.4 mmol) of Cs2CO3 in 6 mL of acetonitrile was stirred at r.t. for 18 hr. The reaction was diluted with aqueous NH4OAc 25% w/v (50 mL) and the mixture was extracted with EtOAc. The organic layer was dried over MgSO4 and concentrated. The resulting residue was purified by chromatography on silica gel eluted with 25-30 % EtOAc in hexane to give the title compound as a colorless gum.

후처리

  1. extractionthe mixture was extracted with EtOAc
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated
  4. customThe resulting residue was purified by chromatography on silica gel
  5. washeluted with 25-30 % EtOAc in hexane

출처 및 근거

ORD 기록
ord-83da7649d3774bdc9206a679240a3b34
출처 데이터셋
uspto-grants-1994_12
특허 번호
US05374635

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