Cesium carbonate → HCID 178489053, compound

HRID 2173933Notes

Reaction equation

HRID 2173933 reaction equation
[C:1]([C:3]1[CH:31]=[CH:30][C:6]2[NH:7][C:8]([CH2:10][C:11]3[C:19]([O:20][CH3:21])=[CH:18][C:17]([CH3:22])=[C:16]4[C:12]=3[CH:13]=[CH:14][N:15]4C(OC(C)(C)C)=O)=[N:9][C:5]=2[CH:4]=1)#[N:2].C([O-])([O-])=O.[Cs+].[Cs+]>C1COCC1.CO>[CH3:21][O:20][C:19]1[C:11]([CH2:10][C:8]2[NH:7][C:6]3[CH:30]=[CH:31][C:3]([C:1]#[N:2])=[CH:4][C:5]=3[N:9]=2)=[C:12]2[C:16](=[C:17]([CH3:22])[CH:18]=1)[NH:15][CH:14]=[CH:13]2

Participants

5

Reactant 2

HCID 10796Cesium carbonateHCID 178488595tert-Butyl 4-((5-cyano-1H-benzo[d]imidazol-2-yl)methyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate

Product 1

HCID 178489053HCID 178489053, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
58 °C

Procedure

To a solution of tert-butyl 4-((5-cyano-1H-benzo[d]imidazol-2-yl)methyl)-5-methoxy-7-methyl-1H-indole-1-carboxylate (878 mg, 2.108 mmol) in THF (12 mL) and MeOH (12 mL) was added Cs2CO3 (3.4 g, 10.54 mmol). The mixture was stirred at 58° C. for 1 hour. The reaction mixture was cooled to room temperature, concentrated and purified by flash chromatography (DCM:EtOAc) to provide the title compound. 1H NMR (400 MHz, DICHLOROMETHANE-d2) δ ppm 8.24 (br. s., 1H) 7.86 (s, 1H) 7.59 (d, J=8.34 Hz, 1H) 7.46-7.54 (m, 1H) 7.30 (t, J=2.91 Hz, 1H) 6.87 (s, 1H) 6.71 (m, 1H) 4.60 (s, 2H) 4.03 (s, 3H) 2.53 (s, 3H). HRMS calcd. for C13H16N4O (M+H)+ 317.1397. found 317.1400.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated
  3. custompurified by flash chromatography (DCM:EtOAc)

Sources & evidence

ORD record
ord-bf0e9b08150a49a9a8969f4518212cea
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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