Triethylamine → HCID 86656170, compound

HRID 1192484Notes

Reaction equation

HRID 1192484 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9]([CH:18](O)[CH3:19])=[CH:10][CH:11]=[C:12]3[C:17]=2[N:16]=[CH:15][CH:14]=[CH:13]3)[CH:5]=[N:6][CH:7]=1.FC1C=C(B(O)O)C=NC=1.C(N(CC)CC)C.CS(Cl)(=O)=O.[N-:43]=[N+:44]=[N-:45].[Na+]>C(Cl)Cl.C(OCC)(=O)C>[N:43]([CH:18]([C:9]1[C:8]([C:4]2[CH:5]=[N:6][CH:7]=[C:2]([F:1])[CH:3]=2)=[C:17]2[C:12]([CH:13]=[CH:14][CH:15]=[N:16]2)=[CH:11][CH:10]=1)[CH3:19])=[N+:44]=[N-:45]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 33557Sodium AzideHCID 44717403(5-Fluoropyridin-3-yl)boronic acidHCID 67248675HCID 67248675, compound

Product 1

HCID 86656170HCID 86656170, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 1-[8-(5-fluoropyridin-3-yl)quinolin-7-yl]ethanol (0.135 g, 0.503 mmol) (prepared in analogy to Example 7 step 1-4, using 5-fluoropyridin-3-ylboronic acid instead of (2-fluorophenypboronic acid as starting material) in methylene chloride (3 mL) was added triethylamine (0.105 mL, 0.755 mmol), followed by methanesulfonyl chloride (0.0487 mL, 0.629 mmol). After stirring at room temperature for 30 minutes, the resultant mixture was diluted with dichloromethane, washed with saturated sodium bicarbonate, brine, dried over magnesium sulfate, then concentrated to dryness under reduced pressure. The crude mesylate was dissolved in N,N-dimethylformamide (2 mL) and treated with sodium azide (0.164 g, 2.52 mmol) at room temperature overnight. After diluting with ethyl acetate, the mixture was washed with water and brine, dried over magnesium sulfate and then evaporated to dryness. The crude product was used in the next step. LCMS calculated for C16H13FN5(M+H)+: m/z=294.1; found: 294.0.

Workup

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

Sources & evidence

ORD record
ord-15aeb113ea214b0ea835390ac4f03ad7
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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