Dimethylformamide → HCID 86656169, compound

HRID 1192482Notes

Reaction equation

HRID 1192482 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]=[CH:6][CH:7]=1.FC1C=C(B(O)O)C=CC=1.C(N(CC)CC)C.CS(Cl)(=O)=O.S([O-])(=O)(=O)C.CN(C)C=O.[N-:53]=[N+:54]=[N-:55].[Na+]>C(Cl)Cl.C(OCC)(=O)C>[N:53]([CH:18]([C:9]1[C:8]([C:4]2[CH:5]=[CH: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+:54]=[N-:55]

Participants

10

Reactant 7

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 33557Sodium AzideHCID 85257MethanesulfonateHCID 27339863-Fluorophenylboronic acidHCID 67247232HCID 67247232, compound

Product 1

HCID 86656169HCID 86656169, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 1-[8-(3-fluorophenyl)quinolin-7-yl]ethanol (0.160 g, 0.598 mmol) (prepared in analogy to Example 7 step 1-4, using (3-fluorophenyl)boronic acid instead of (2-fluorophenyl)boronic acid as starting material) in methylene chloride (4 mL) was added triethylamine (0.125 mL, 0.898 mmol), followed by methanesulfonyl chloride (0.0579 mL, 0.748 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 crude mesylate was dissolved in N,N-dimethylformamide (2 mL, 20 mmol) and treated with sodium azide (0.194 g, 2.99 mmol) at room temperature overnight. After diluted 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 C17H14FN4(M+H)+: m/z=293.1; found: 293.0.

Workup

  1. customprepared in analogy to Example 7 step 1-4
  2. washwashed with saturated sodium bicarbonate and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated to dryness under reduced pressure
  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-f02d7a6790314547bc4d9bc4e1f2fad5
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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