Cesium carbonate → HCID 71766101, compound

HRID 1054858Notes

Reaction equation

HRID 1054858 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 1.0 M 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-1dee0c75a5a44034b684d9b0e9cdace7
Source dataset
uspto-grants-2016_07
Patent number
US09394285B2

Reaction notes

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