Cesium carbonate → HCID 19789802, compound

HRID 1655970Notes

Reaction equation

HRID 1655970 reaction equation
[Cl:1][C:2]1[CH:31]=[CH:30][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]([S:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[C:8]2[CH2:22][C:23]([CH3:29])([CH3:28])[C:24]([O:26][CH3:27])=[O:25])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:39][C:40]1[CH:49]=[CH:48][C:47]2[C:42](=[CH:43][CH:44]=[C:45]([F:50])[CH:46]=2)[N:41]=1>C(#N)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH2:39][C:40]4[CH:49]=[CH:48][C:47]5[C:42](=[CH:43][CH:44]=[C:45]([F:50])[CH:46]=5)[N:41]=4)=[CH:13][CH:14]=3)[C:9]([S:17][C:18]([CH3:20])([CH3:19])[CH3:21])=[C:8]2[CH2:22][C:23]([CH3:29])([CH3:28])[C:24]([O:26][CH3:27])=[O:25])=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 14980577Methyl 3-(3-(tert-butylthio)-1-(4-chlorobenzyl)-5-hydroxy-1H-indol-2-yl)-2,2-dimethylpropanoateHCID 216180422-(Bromomethyl)-6-fluoroquinoline

Product 1

HCID 19789802HCID 19789802, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of Methyl 3-[N-(p-chlorobenzyl)-3-(t-butylthio)-5-hydroxyindol-2-yl]-2,2-dimethylpropanoate (See EP419,049, Example 1, Step C) (322 mg) in acetonitrile (7 mL) were added solid cesium carbonate (456 mg) and 2-bromomethyl-6-fluoroquinoline (190 mg) from Step A. The mixture was stirred at room temperature for 18 hr. The mixture was poured into 25% aqueous NH4OAc (50 mL), extracted with ethyl acetate (2×50 mL), washed with brine (50 mL), dried (MgSO4) and evaporated to dryness. The residue was chromatographed on flash silica gel using ethyl acetate:toluene (5:95) as eluant to give the title compound as a white solid; m.p. 165°-167° C.

Workup

  1. extractionextracted with ethyl acetate (2×50 mL)
  2. washwashed with brine (50 mL)
  3. dry with materialdried (MgSO4)
  4. customevaporated to dryness
  5. customThe residue was chromatographed on flash silica gel

Sources & evidence

ORD record
ord-47f2dd8fc7444ecfb8dac60422586b09
Source dataset
uspto-grants-1993_10
Patent number
US05252585

Reaction notes

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