Sodium Iodide → HCID 25106898, compound

HRID 1624894Notes

Reaction equation

HRID 1624894 reaction equation
C[O:2][C:3]1[CH:8]=[N:7][N:6]([C:9]2[CH:10]=[C:11]([NH:15][C:16](=[O:18])[CH3:17])[CH:12]=[CH:13][CH:14]=2)[C:5](=[O:19])[N:4]=1.Br[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=1[F:29].[I-].[Na+]>C(#N)C>[Cl:28][C:25]1[CH:26]=[CH:27][C:22]([CH2:21][N:4]2[C:3](=[O:2])[CH:8]=[N:7][N:6]([C:9]3[CH:10]=[C:11]([NH:15][C:16](=[O:18])[CH3:17])[CH:12]=[CH:13][CH:14]=3)[C:5]2=[O:19])=[C:23]([F:29])[CH:24]=1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 27365514-Chloro-2-fluorobenzyl bromideHCID 68703823HCID 68703823, compound

Product 1

HCID 25106898HCID 25106898, compoundYield 22.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

According to Scheme 6 Step 2: To a stirred solution of N-(3-(5-methoxy-3-oxo-1,2,4-triazin-2(3H)-yl)phenyl)acetamide (40 mg, 0.15 mmol) in acetonitrile (3 mL) were added 1-(bromomethyl)-4-chloro-2-fluorobenzene (52 mg, 0.23 mmol) and sodium iodide (46 mg, 0.31 mmol). The mixture was heated irradiated at 160° C. under microwave irradiation. The reaction mixture was quenched with water and extracted with ethyl acetate (×3). The combined organic layers were successively washed with water then with brine, dried over MgSO4, filtered and concentrated. The crude product was purified by flash chromatography, 5 g column, CH2Cl2/MeOH 98/2 to afford the N-(3-(4-(4-chloro-2-fluorobenzyl)-3,5-dioxo-4,5-dihydro-1,2,4-triazin-2(3H)-yl)phenyl)acetamide 10(B) as a yellow solid (13 mg, 22%).

Workup

  1. temperatureThe mixture was heated
  2. customirradiated at 160° C. under microwave irradiation
  3. customThe reaction mixture was quenched with water
  4. extractionextracted with ethyl acetate (×3)
  5. washThe combined organic layers were successively washed with water
  6. dry with materialwith brine, dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product was purified by flash chromatography, 5 g column, CH2Cl2/MeOH 98/2

Sources & evidence

ORD record
ord-d8a643ce24494542a76d68d3ab283b61
Source dataset
uspto-grants-2014_07
Patent number
US08779129B2

Reaction notes

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