Реакция #7271

Уравнение реакции

1-(2-trimethylsilylethoxymethyl)-2-formyl-benzimidazole

N′-(1H-benzimidazol-2-ylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine

sodium borohydride

→

desired product

Выход 47.0%

(1H-Benzimidazol-2-ylmethyl)-(4-{[(1H-benzimidazol-2-ylmethyl)-amino]-methyl}-benzyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine

Выход 47.0%

Растворители

MeOH

MeOH

Условия реакции

Обработка

1. 1
   Концентрированиеthen concentrated under reduced pressure
2. 2
   workup.DISSOLUTIONThe residue was dissolved in dry MeOH (5 mL) and to the resultant solution
3. 3
   workup.STIRRINGthe reaction mixture stirred for 16 h (see General Procedures XX)
4. 4
   ДругоеPurification of the crude product by radial chromatography on a 2 mm TLC grade silica gel plate (CH2Cl2/MeOH/NH4OH, 100:1:1 followed by 50:1:1)

Методика

To a stirred solution of 1-(2-trimethylsilylethoxymethyl)-2-formyl-benzimidazole (prepared as described by Bridger et al. U.S. patent application Ser. No. 09/535,314) (0.150 g, 0.54 mmol) in dry MeOH (2.5 mL) was added a dry MeOH (2.5 mL) solution of N′-(1H-benzimidazol-2-ylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine (0.215 g, 0.54 mmol) under an argon atmosphere. The mixture was stirred at room temperature for 1.5 h then concentrated under reduced pressure and analyzed by 1H NMR. The residue was dissolved in dry MeOH (5 mL) and to the resultant solution was added sodium borohydride (41 mg, 1.08 mmol) and the reaction mixture stirred for 16 h (see General Procedures XX). Purification of the crude product by radial chromatography on a 2 mm TLC grade silica gel plate (CH2Cl2/MeOH/NH4OH, 100:1:1 followed by 50:1:1) afforded the desired product (0.165 g, 47%) as a pale yellow oil.

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