Iodoethane → HCID 67234021, compound

HRID 876396Notes

Reaction equation

HRID 876396 reaction equation
[N:1]1[N:2]=[C:3]([C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[C:13]([O:20][CH2:21][C:22]([CH3:33])([CH3:32])[CH2:23][NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[CH:14]=[CH:15][CH:16]=3)[N:11]=2)[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.[H-].[Na+].[CH2:36](I)[CH3:37].[NH4+].[Cl-]>CN(C=O)C>[N:1]1[N:2]=[C:3]([C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[C:13]([O:20][CH2:21][C:22]([CH3:33])([CH3:32])[CH2:23][N:24]([CH2:36][CH3:37])[C:25](=[O:31])[O:26][C:27]([CH3:28])([CH3:30])[CH3:29])[CH:14]=[CH:15][CH:16]=3)[N:11]=2)[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12

Participants

6

Reactant 4

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 67234600HCID 67234600, compound

Product 1

HCID 67234021HCID 67234021, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of tert-butyl 3-(2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yloxy)-2,2-dimethylpropylcarbamate (50 mg, 0.11 mmol) in anhydrous DMF (2 mL) was added NaH (7 mg, 60%, 0.17 mmol). After stirring at ambient temperature for 20 min, ethyl iodide (27 μL, 0.34 mmol) was added and the mixture stirred for a further 5 hrs. The mixture was treated with saturated NH4Cl (20 mL) and extracted with EtOAc (3×10 mL). The combined organic phases were washed with water and brine and concentrated to afford a yellow gum. The residue was purified by flash column chromatography using gradient elution (CH2Cl2 to 1% MeOH/CH2Cl2 to 2% MeOH/CH2Cl2) to afford desired product (45 mg, 85%) as a colorless gum.

Workup

  1. stirringthe mixture stirred for a further 5 hrs
  2. extractionextracted with EtOAc (3×10 mL)
  3. washThe combined organic phases were washed with water and brine
  4. concentrationconcentrated
  5. customto afford a yellow gum
  6. customThe residue was purified by flash column chromatography
  7. washelution (CH2Cl2 to 1% MeOH/CH2Cl2 to 2% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-2c39136e6ca147658a9e2845d54b121a
Source dataset
uspto-grants-2015_03
Patent number
US08987251B2

Reaction notes

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