Cesium carbonate → HCID 15228773, compound

HRID 1741779Notes

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+].CS(O[CH:43]([C:45]1[CH:54]=[CH:53][C:52]2[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=2)[N:46]=1)[CH3:44])(=O)=O>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][CH:43]([C:45]4[CH:54]=[CH:53][C:52]5[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=5)[N:46]=4)[CH3:44])=[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

Conditions

Temperature: 70 °C

Procedure

To a solution of methyl 3-[N-(p-chlorobenzyl)-3-(t-butylthio)-5-hydroxy-indol-2-yl]-2,2-dimethylpropanoate (EP 419,049, Example 1, Step C) (460 mg) in acetonitrile (5 mL) was added solid cesium carbonate (652 mg). To this mixture was added a solution of mesylate from Step B (326 mg) in acetonitrile (3 mL) and stirred at 70° C. for 1 hr. The reaction mixture was poured into 25% NH4OAc (50 mL), extracted with ethyl acetate (2×50 mL), washed with brine (50 mL), and dried (MgSO4). The solution was evaporated to dryness and the residue was chromatographed on flash silica gel using ethyl acetate:hexane (1:4) as eluant to give the title compound identical to the one obtained from Method 1, Step A.

Workup

extractionextracted with ethyl acetate (2×50 mL)
washwashed with brine (50 mL)
dry with materialdried (MgSO4)
customThe solution was evaporated to dryness
customthe residue was chromatographed on flash silica gel

Sources & evidence

ORD record: ord-4a7f5dc369cb4a9e9a8e276d68e5b1f0
Source dataset: uspto-grants-1994_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05334719

Reaction notes

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