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

HRID 1492412Notes

Reaction equation

HRID 1492412 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-83da7649d3774bdc9206a679240a3b34
Source dataset
uspto-grants-1994_12
Patent number
US05374635

Reaction notes

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