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

HRID 274418Notes

Reaction equation

HRID 274418 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-5a87c71a46ea426eb8635a9f01235f3b
Source dataset
uspto-grants-1995_02
Patent number
US05389650

Reaction notes

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