Triethylamine → 7-(1-Azidoethyl)-5-chloro-8-(2-fluorophenyl)quinoline

HRID 1192491Notes

Reaction equation

HRID 1192491 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([CH:12](O)[CH3:13])[C:9]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[F:21])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.C(N(CC)CC)C.CS(Cl)(=O)=O.[N-:34]=[N+:35]=[N-:36].[Na+]>C(Cl)Cl.C(OCC)(=O)C>[N:34]([CH:12]([C:10]1[C:9]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[F:21])=[C:8]2[C:3]([CH:4]=[CH:5][CH:6]=[N:7]2)=[C:2]([Cl:1])[CH:11]=1)[CH3:13])=[N+:35]=[N-:36]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 33557Sodium AzideHCID 672484331-[5-Chloro-8-(2-fluorophenyl)quinolin-7-yl]ethanol

Product 1

HCID 866561747-(1-Azidoethyl)-5-chloro-8-(2-fluorophenyl)quinoline

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 1-[5-chloro-8-(2-fluorophenyl)quinolin-7-yl]ethanol (0.044 g, 0.14 mmol) in methylene chloride (0.9 mL) was added triethylamine (0.0305 mL, 0.219 mmol), followed by methanesulfonyl chloride (0.0141 mL, 0.182 mmol). After stirring at room temperature for 30 minutes, the resultant mixture was diluted with dichloromethane, washed with saturated sodium bicarbonate and brine, dried over magnesium sulfate, and then concentrated to dryness under reduced pressure. The resulting residue was used directly in next step. LCMS (M+H)+m/z=380.0. The crude mesylate was dissolved in N,N-dimethylformamide (0.4 mL) and treated with sodium azide (0.0474 g, 0.730 mmol) at 60° C. for 1 hour. After diluting with ethyl acetate, the mixture was washed with water and brine and then dried over magnesium sulfate and evaporated to dryness. The crude product was used in the next step. LCMS calculated for C17H13ClFN4(M+H)+: m/z=327.1; found: 327.0.

Workup

  1. washwashed with saturated sodium bicarbonate and brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated to dryness under reduced pressure
  4. dissolutionThe crude mesylate was dissolved in N,N-dimethylformamide (0.4 mL)
  5. washthe mixture was washed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-4d359eae8a9d46fe94eec461379a36e6
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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