Cesium carbonate → HCID 71766101, compound

HRID 338514Notes

Reaction equation

HRID 338514 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:18]([O:20]C)=[O:19])=[CH:7][N:8]2C(OC(C)(C)C)=O)=[CH:4][C:3]=1[C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1.Cl[CH2:30][CH2:31][N:32]1[CH:36]=[N:35][CH:34]=[N:33]1.C(=O)([O-])[O-].[Cs+].[Cs+].[OH-].[Na+]>CO.O1CCCC1>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:18]([OH:20])=[O:19])=[CH:7][NH:8]2)=[CH:4][C:3]=1[C:22]1[CH:27]=[CH:26][C:25]([O:28][CH2:30][CH2:31][N:32]2[CH:36]=[N:35][CH:34]=[N:33]2)=[CH:24][CH:23]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 14798Sodium HydroxideHCID 47122751-(2-chloroethyl)-1H-1,2,4-triazoleHCID 86698779HCID 86698779, compound

Product 1

HCID 71766101HCID 71766101, compoundYield 3.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A vial was charged with 1-tert-butyl 3-methyl 6-chloro-5-(4-hydroxyphenyl)-1H-indole-1,3-dicarboxylate (30 mg, 0.075 mmol), 1-(2-chloroethyl)-1H-1,2,4-triazole (15 mg, 0.12 mmol) and tetrahydrofuran (1 mL). Cesium carbonate (64 mg, 0.18 mmol) was then added and the vial was sealed and stirred at room temperature for 3 hours then heated to 70° C. for 18 h. The reaction was filtered and the filtrate was concentrated in vacuo. Methanol (1 mL) and 1.0M sodium hydroxide (0.3 mL, 0.3 mmol) were added and the reaction stirred for 18 h at 70° C. The reaction was then concentrated in vacuo and purified by reverse phase HPLC to provide 1 mg of the title compound. MS (ES+) 383.1 (M+H)+. Retention time=2.38 minutes (Waters Atlantis dC18 4.6×50, 5 μm; Mobile phase A: 0.05% TFA in water (v/v); Mobile phase B: 0.05% TFA in MeCN (v/v); Gradient: 95:5 A:B linear to 5:95 A:B in 4.0 min, hold at 5:95 A:B to 5.0 min. Flow: 2 mL/min).

Workup

  1. customthe vial was sealed
  2. temperaturethen heated to 70° C. for 18 h
  3. filtrationThe reaction was filtered
  4. concentrationthe filtrate was concentrated in vacuo
  5. stirringthe reaction stirred for 18 h at 70° C
  6. concentrationThe reaction was then concentrated in vacuo
  7. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-fb63c6e7248a4e96a8e7c209afef7311
Source dataset
uspto-grants-2014_11
Patent number
US08889730B2

Reaction notes

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