1-Methylimidazole → HCID 68324141, compound

HRID 573653Notes

Reaction equation

HRID 573653 reaction equation
Br[C:2]1[S:22][C:5]2=[N:6][C:7]([CH3:21])=[CH:8][C:9]([NH:10][S:11]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=3)(=[O:13])=[O:12])=[C:4]2[C:3]=1[CH3:23].[CH3:24][N:25]1C=CN=C1>[Fe-4](C#N)(C#N)(C#N)(C#N)(C#N)C#N.[K+].[K+].[K+].[K+].[Cu]I>[Cl:20][C:16]1[CH:15]=[C:14]([S:11]([NH:10][C:9]2[CH:8]=[C:7]([CH3:21])[N:6]=[C:5]3[S:22][C:2]([C:24]#[N:25])=[C:3]([CH3:23])[C:4]=23)(=[O:13])=[O:12])[CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 2

HCID 13901-MethylimidazoleHCID 68324042N-(2-bromo-3,6-dimethylthieno[2,3-b]pyridin-4-yl)-3-chlorobenzenesulfonamide

Product 1

HCID 68324141HCID 68324141, compoundYield 28.6%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178511492HCID 178511492, compoundCatalyst

Conditions

Temperature
160 °C

Procedure

To a solution of N-(2-bromo-3,6-dimethylthieno[2,3-b]pyridin-4-yl)-3-chlorobenzenesulfonamide (Example 77) (100 mg, 0.232 mmol) in 1-methylimidazole (1.5 mL, 18.82 mmol) was added potassium ferrocyanide (17.06 mg, 0.046 mmol) and copper(I) iodide (4.41 mg, 0.023 mmol) and the reaction stirred at 160° C. for 16 h. The reaction mixture was then cooled to RT before directly purifying on silica, eluting with a gradient of 0-20% 2M NH3 in MeOH in DCM. Further purification by MDAP (acidic conditions), afforded the title compound (25.1 mg). LCMS (A) m/z: 378 [M+1]+, Rt 1.10 min (acidic).

Workup

  1. temperatureThe reaction mixture was then cooled to RT
  2. custombefore directly purifying on silica
  3. washeluting with a gradient of 0-20% 2M NH3 in MeOH in DCM
  4. customFurther purification by MDAP (acidic conditions)

Sources & evidence

ORD record
ord-e4988729f42840f685b9e5eedf45bc35
Source dataset
uspto-grants-2015_05
Patent number
US09029545B2

Reaction notes

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