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

HRID 274418노트

반응식

HRID 274418 반응식
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([OH:16])=[CH:13][CH:14]=3)[C:9]([CH3:17])=[C:8]2[CH2:18][C:19]([CH3:25])([CH3:24])[C:20]([O:22][CH3:23])=[O:21])=[CH:4][CH:3]=1.[C:28]1([C:34]2[CH:35]=[CH:36][C:37]([CH2:40]Br)=[N:38][CH:39]=2)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C([O-])([O-])=O.[K+].[K+].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH2:40][C:37]4[CH:36]=[CH:35][C:34]([C:28]5[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=5)=[CH:39][N:38]=4)=[CH:13][CH:14]=3)[C:9]([CH3:17])=[C:8]2[CH2:18][C:19]([CH3:24])([CH3:25])[C:20]([O:22][CH3:23])=[O:21])=[CH:4][CH:3]=1

참가 물질

6

반응물 4

HCID 10796Cesium carbonateHCID 11430Potassium CarbonateHCID 151713012-(Bromomethyl)-5-phenylpyridineHCID 15229448HCID 15229448, 화합물

생성물 1

HCID 15229449Methyl 3-[1-(4-Chlorobenzyl)-3-methyl-5-(5-phenylpyridin-2-ylmethoxy)indol-2-yl]-2,2-dimethylpropanoate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of methyl 3-[1-(4-chlorobenzyl)-3-methyl-5-hydroxyindol-2-yl]-2,2-dimethylpropanoate (180 mg) (Preparation 1), 5-phenyl-2-picolyl bromide (138 mg), K2CO3 (84 mg) and Cs2CO3 (30 mg) in DMF (5 mL) wase stirred at r.t. under nitrogen for 48 hours. The mixture was poured onto 1N HCL, extracted 2× EtOAc, washed 2× brine, dried (MgSO4), and evaporated to dryness. The residue was purified by column chromatography (hexane/EtOAc 5:1 then 1:1) to give the title compound.

후처리

  1. additionThe mixture was poured onto 1N HCL
  2. extractionextracted 2× EtOAc
  3. washwashed 2× brine
  4. dry with materialdried (MgSO4)
  5. customevaporated to dryness
  6. customThe residue was purified by column chromatography (hexane/EtOAc 5:1

출처 및 근거

ORD 기록
ord-5a87c71a46ea426eb8635a9f01235f3b
출처 데이터셋
uspto-grants-1995_02
특허 번호
US05389650

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