1,4-Dioxane → 1-(6-Fluoro-3,4-di(pyridin-2-yl)quinolin-2-yl)ethanamine

HRID 1616062Notes

Reaction equation

HRID 1616062 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH:12]([NH:14]C(=O)OC(C)(C)C)[CH3:13])[C:6]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=1)=[C:5]2[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=1.O1CCOCC1>Cl>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH:12]([NH2:14])[CH3:13])[C:6]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=1)=[C:5]2[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=1

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 67595333Tert-butyl 1-(6-fluoro-3,4-di(pyridin-2-yl)quinolin-2-yl)ethylcarbamate

Product 1

HCID 696731471-(6-Fluoro-3,4-di(pyridin-2-yl)quinolin-2-yl)ethanamine

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of tert-butyl 1-(6-fluoro-3,4-di(pyridin-2-yl)quinolin-2-yl)ethylcarbamate (0.4146 g, 0.933 mmol) was dissolved in hydrochloric acid, 4 M solution in 1,4-dioxane (4.66 mL, 18.65 mmol) and the mixture was stirred at rt. After 3.5 h, the mixture was partitioned between DCM (50 mL) and water (50 mL). The acidic aq mixture was washed with DCM (30 mL×2) to remove organic impurities and then basified to ˜pH 10 with 10 N NaOH (3.5 mL), extracted with DCM (50 mL×3). The combined organic layers were washed with water (100 mL×1), brine (100 mL×1), dried over MgSO4, filtered, and concentrated in vacuo to give 1-(6-fluoro-3,4-di(pyridin-2-yl)quinolin-2-yl)ethanamine as an orange syrup: LC-MS (ESI) m/z 345.1 [M+H]+. The orange syrup was carried on crude without further purification.

Workup

  1. customthe mixture was partitioned between DCM (50 mL) and water (50 mL)
  2. washThe acidic aq mixture was washed with DCM (30 mL×2)
  3. customto remove organic impurities
  4. extractionextracted with DCM (50 mL×3)
  5. washThe combined organic layers were washed with water (100 mL×1), brine (100 mL×1)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d81da99867c34e9b976911bf44a2c4d9
Source dataset
uspto-grants-2014_07
Patent number
US08765768B2

Reaction notes

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