Tetrahydrofuran → HCID 178504206, compound

HRID 60267Notes

Reaction equation

HRID 60267 reaction equation
Cl[C:2]1[C:10]2[C:9]3[CH:11]=[C:12]([C:15]#[N:16])[N:13]=[CH:14][C:8]=3[N:7]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[C:6]=2[N:5]=[CH:4][CH:3]=1.[H-].[Na+].[O:27]1CCCC1>O.C(OCC)(=O)C>[OH:27][C:2]1[C:10]2[C:9]3[CH:11]=[C:12]([C:15]#[N:16])[N:13]=[CH:14][C:8]=3[N:7]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[C:6]=2[N:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 582666684-Chloro-9-(2-trimethylsilanyl-ethoxymethyl)-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carbonitrile

Product 1

HCID 178504206HCID 178504206, compound

Reagents, catalysts & solvents 3

HCID 962WaterCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-chloro-9-(2-trimethylsilanyl-ethoxymethyl)-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile (100 mg, 0.3 mmol) in tetrahydrofuran (1.8 mL) was added sodium hydride as a 60% dispersion in mineral oil (22 mg, 0.56 mmol) followed by a few drops of water. The reaction mixture was stirred at ambient temperature for 5 minutes and then at 40° C. for 2 hours. The mixture was diluted with water (20 mL) and ethyl acetate (50 mL). The organic layer was separated, dried over sodium sulfate, filtered, concentrated in vacuo, and purified flash chromatography (silica, 4 g, ISCO, 5-100% ethyl acetate in heptane) to afford the title compound as a pale yellow oil, which was used in the next step without any further purification (70 mg).

Workup

  1. waitat 40° C. for 2 hours
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. custompurified flash chromatography (silica, 4 g, ISCO, 5-100% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-5b20dbe7f77841dfa75b1479d2b1f97e
Source dataset
uspto-grants-2016_09
Patent number
US09440976B2

Reaction notes

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