Cesium carbonate → Methyl 3-[1-(4-chlorobenzyl)-3-(t-butylthio)-5-(1,6-naphthyridin-2-ylmethoxy)indol-2-yl]-2,2-dimethylpropanoate

HRID 327409Notes

Reaction equation

HRID 327409 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+].Cl[CH2:39][C:40]1[CH:49]=[CH:48][C:47]2[C:42](=[CH:43][CH:44]=[N:45][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]=[N:45][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 191085252-Chloromethyl-1,6-naphthyridine

Product 1

HCID 19108529Methyl 3-[1-(4-chlorobenzyl)-3-(t-butylthio)-5-(1,6-naphthyridin-2-ylmethoxy)indol-2-yl]-2,2-dimethylpropanoate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of methyl 3-[1-(4-chlorobenzyl)-3-(t-butylthio)-5-hydroxyindol-2-yl]-2,2-dimethylpropanoate (EP 419,049, Mar. 27, 1991, Example 1, Step C) (350 mg) in acetonitrile (5 mL) were added Cs2CO3 (489 mg) and 80% pure halide (180 mg) from Step 1. The mixture was stirred at room temperature for 18 hr. then the mixture was poured into 25% aq. NH4OAc (50 mL), extracted with ethyl acetate (2×50 mL), washed with brine (50 mL), dried (MgSO4), and evaporated to dryness. Chromatography of the residue on flash silica gel using ethyl acetate:toluene (2:3) as eluant gave the title compound as a white solid; m.p. 152°-155° 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

Sources & evidence

ORD record
ord-6300ef0fc4cb4e22b4584b9cf13b47e2
Source dataset
uspto-grants-1993_12
Patent number
US05273980

Reaction notes

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