Sodium ethoxide → 3-(2,4-Dimethylphenyl)-6-(pyridin-2-ylmethylthio)pyridazine

HRID 1625567Notes

Reaction equation

HRID 1625567 reaction equation
Br.Br[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1.[CH3:10][C:11]1[CH:16]=[C:15]([CH3:17])[CH:14]=[CH:13][C:12]=1[C:18]1[CH:19]=[CH:20][C:21](=[S:24])[NH:22][N:23]=1.CC[O-].[Na+]>CCO>[CH3:10][C:11]1[CH:16]=[C:15]([CH3:17])[CH:14]=[CH:13][C:12]=1[C:18]1[N:23]=[N:22][C:21]([S:24][CH2:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=2)=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 2723922Sodium ethoxideHCID 27347202-(Bromomethyl)pyridine hydrobromideHCID 125621006-(2,4-Dimethylphenyl)pyridazine-3-thiol

Product 1

HCID 405320433-(2,4-Dimethylphenyl)-6-(pyridin-2-ylmethylthio)pyridazineYield 35%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 2-(bromomethyl)pyridine hydrobromide (116 mg; 0.46 mmol) and 6-(2,4-dimethylphenyl)pyridazine-3(2H)-thione (Example 13a) (100 mg, 0.46 mmol) in EtOH (3 mL) was added EtONa (20% in EtOH, 25 μl) and the reaction was irradiated in a microwave at 140° C. for 4 min. The crude mixture was dried down and purified on silica gel (Eluent: 5% MeOH in DCM) to give 3-(2,4-Dimethylphenyl)-6-(pyridin-2-ylmethylthio)pyridazine (49 mg, 35%) as a white solid solid. 1H NMR (300 MHz, dMSO: δ 2.49 (s, 3H), 2.54 (s, 3H), 4.09 (s, 2H), 6.32-6.37 (m, 2H), 6.45-6.52 (m, 2H), 6.75-6.78 (d, 1H), 6.84-6.87 (m, 2H), 6.95-6.98 (t, 1H), 7.67-7.68 (d, 1H); MS (M+H, 308).

Workup

  1. customthe reaction was irradiated in a microwave at 140° C. for 4 min
  2. dry with materialThe crude mixture was dried down
  3. custompurified on silica gel (Eluent: 5% MeOH in DCM)

Sources & evidence

ORD record
ord-bc417a0fa2314381892e6b2bbdaf4d76
Source dataset
uspto-grants-2014_07
Patent number
US08784782B2

Reaction notes

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