Sodium ethoxide → HCID 178429692, compound

HRID 2173922Notes

Reaction equation

HRID 2173922 reaction equation
[F:1][C:2]([F:41])([F:40])[C:3]([C:29]1[NH:33][C:32]2[CH:34]=[CH:35][C:36]([C:38]#[N:39])=[CH:37][C:31]=2[N:30]=1)([OH:28])[C:4]1[C:12]([S:13]([CH3:16])(=[O:15])=[O:14])=[CH:11][C:10]([CH3:17])=[C:9]2[C:5]=1[CH:6]=[CH:7][N:8]2S(C1C=CC(C)=CC=1)(=O)=O.[O-]CC.[Na+]>CCO>[F:41][C:2]([F:1])([F:40])[C:3]([C:29]1[NH:33][C:32]2[CH:34]=[CH:35][C:36]([C:38]#[N:39])=[CH:37][C:31]=2[N:30]=1)([OH:28])[C:4]1[C:12]([S:13]([CH3:16])(=[O:15])=[O:14])=[CH:11][C:10]([CH3:17])=[C:9]2[C:5]=1[CH:6]=[CH:7][NH:8]2

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 178427343HCID 178427343, compound

Product 1

HCID 178429692HCID 178429692, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-(2,2,2-trifluoro-1-hydroxy-1-(7-methyl-5-(methylsulfonyl)-1-tosyl-1H-indol-4-yl)ethyl)-1H-benzo[d]imidazole-5-carbonitrile (187 mg, 0.310 mmol) in EtOH (3103 μL) was added sodium ethoxide (21% in EtOH, 2.3 mL, 6.21 mmol) and the mixture was stirred at 60° C. After 2 hours the reaction was cooled to room temperature and stirred overnight. The mixture was concentrated and then purified directly by flash chromatography (0-100% EtOAc in heptanes) to provide the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.64-12.79 (m, 1H) 11.60 (br. s., 1H) 8.38-8.49 (m) 8.05 (s, 1H) 7.97-8.03 (m) 7.89 (m) 7.58-7.66 (m, 1H) 7.48-7.55 (m) 7.18-7.32 (m, 1H) 5.61 (br. s., 1H) 3.52 (s, 3H) 2.57 (s, 3H). HRMS calcd. for C20H16F3N4O3S (M+H)+ 449.0895. found 449.0889.

Workup

  1. temperatureAfter 2 hours the reaction was cooled to room temperature
  2. stirringstirred overnight
  3. concentrationThe mixture was concentrated
  4. custompurified directly by flash chromatography (0-100% EtOAc in heptanes)

Sources & evidence

ORD record
ord-f7c763acadcb4daba7837bfaad7c6710
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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