Sodium Iodide → HCID 58365165, compound

HRID 60288Notes

Reaction equation

HRID 60288 reaction equation
[CH3:1][C:2]1([CH2:8][O:9][C:10]2[C:18]3[C:17]4[CH:19]=[C:20]([C:23]#[N:24])[N:21]=[CH:22][C:16]=4[N:15]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[C:14]=3[N:13]=[CH:12][CH:11]=2)[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[I-].[Na+].Br[CH2:36][CH2:37][O:38][CH3:39].C(N(CC)C(C)C)(C)C>C(#N)C.C(=O)(O)[O-].[Na+].O.C(Cl)Cl>[CH3:39][O:38][CH2:37][CH2:36][N:5]1[CH2:4][CH2:3][C:2]([CH2:8][O:9][C:10]2[C:18]3[C:17]4[CH:19]=[C:20]([C:23]#[N:24])[N:21]=[CH:22][C:16]=4[N:15]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:31])([CH3:30])[CH3:32])[C:14]=3[N:13]=[CH:12][CH:11]=2)([CH3:1])[CH2:7][CH2:6]1

Participants

9

Reactant 4

HCID 5238Sodium IodideHCID 809722-Bromoethyl methyl ether2×HCID 81531DiisopropylethylamineHCID 67247661HCID 67247661, compound

Product 1

HCID 58365165HCID 58365165, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 4-((4-methylpiperidin-4-yl)methoxy)-9-(2-trimethylsilanyl-ethoxymethyl)-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile (74 mg, 0.16 mmol) in acetonitrile (1.7 mL) was added sodium iodide (26 mg, 0.17 mmol) and 1-bromo-2-methoxyethane (16 uL, 0.17 mmol). The reaction mixture was warmed to 50° C. for 18 hours. The mixture was allowed to cool and then 1-bromo-2-methoxyethane (65 uL, 0.69 mmol) and N,N-diisopropylethylamine (29 uL, 0.16 mmol) were added and the mixture was heated at 50° C. for an additional 4 hours. The cooled reaction mixture was diluted with saturated aqueous sodium bicarbonate solution (10 mL), water (20 mL), and methylene chloride (50 mL). The organic layer was separated, dried over sodium sulfate, filtered, concentrated in vacuo, and purified flash chromatography (silica, 4 g, ISCO, 1-20% methanol in dichloromethane) to afford the title compound as an oil, which was used in the next step without any further purification (36 mg, 43%).

Workup

  1. temperatureto cool
  2. temperaturethe mixture was heated at 50° C. for an additional 4 hours
  3. customThe cooled reaction mixture
  4. customThe organic layer was separated
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. custompurified flash chromatography (silica, 4 g, ISCO, 1-20% methanol in dichloromethane)

Sources & evidence

ORD record
ord-4811cccf6d4d4339bd1b6dbaa5a1aafd
Source dataset
uspto-grants-2016_09
Patent number
US09440976B2

Reaction notes

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