Acetic Acid → (E)-N-benzyl-N-{2-[2-(1H-indazol-3-yl)vinyl]phenyl}amine

HRID 1821321Notes

Reaction equation

HRID 1821321 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[CH:11]/[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[NH2:18])=[N:2]1.[CH:19](=O)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClC(Cl)C.O>[CH2:19]([NH:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1/[CH:11]=[CH:10]/[C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1][N:2]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 69001756HCID 69001756, compound

Product 1

HCID 68998952(E)-N-benzyl-N-{2-[2-(1H-indazol-3-yl)vinyl]phenyl}amineYield 38%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 63651,1-DichloroethaneSolvent

Procedure

(E)-2-[2-(1H-indazol-3-yl)vinyl]phenylamine (60 mg, 0.26 mmol) was dissolved in dichloroethane and the solution was added with benzaldehyde (28 μL, 0.28 mmol), sodium triacetoxyborohydride (81 mg, 0.38 mmol) and acetic acid (15 mL, 0.25 mmol), followed by stirring at room temperature for 13 hours. The reaction mixture was added with water and extracted with ethyl acetate. The organic layer was sequentially washed with water and saturated brine, dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. A crude product was purified by silica gel chromatography [ethyl acetate/hexane=1/8 to 1/1] and further crystallized from ethyl acetate to obtain Compound 26 (31.1 mg, 38%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was sequentially washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customA crude product was purified by silica gel chromatography [ethyl acetate/hexane=1/8 to 1/1]
  6. customfurther crystallized from ethyl acetate

Sources & evidence

ORD record
ord-1bbebaafdc5b46db804bb9581278aa22
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

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