3-Fluoro-4-nitrobenzaldehyde → 2-(4-tert-Butyl-phenyl)-4-[4-(3-fluoro-4-nitro-benzyl)-piperazin-1-yl]-1H-benzoimidazole

HRID 642880노트

반응식

HRID 642880 반응식
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[NH:15][C:14]3[CH:16]=[CH:17][CH:18]=[C:19]([N:20]4[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]4)[C:13]=3[N:12]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[F:26][C:27]1[CH:28]=[C:29]([CH:32]=[CH:33][C:34]=1[N+:35]([O-:37])=[O:36])[CH:30]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CN1CCCC1=O.C(OCC)(=O)C>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[NH:15][C:14]3[CH:16]=[CH:17][CH:18]=[C:19]([N:20]4[CH2:25][CH2:24][N:23]([CH2:30][C:29]5[CH:32]=[CH:33][C:34]([N+:35]([O-:37])=[O:36])=[C:27]([F:26])[CH:28]=5)[CH2:22][CH2:21]4)[C:13]=3[N:12]=2)=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

참가 물질

6

반응물 3

HCID 38081203-Fluoro-4-nitrobenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 592588032-(4-tert-Butyl-phenyl)-4-piperazin-1-yl-1H-benzoimidazole

생성물 1

HCID 585927062-(4-tert-Butyl-phenyl)-4-[4-(3-fluoro-4-nitro-benzyl)-piperazin-1-yl]-1H-benzoimidazole수율 68.1%

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

To a stirring solution of 2-(4-tert-Butyl-phenyl)-4-piperazin-1-yl-1H-benzoimidazole (0.857 g, 2.56 mMol) and 3-Fluoro-4-nitro-benzaldehyde (0.52 g, 3.07 mMol) in N-methylpyrrolidinone (20 mL) was added sodium triacetoxyborohydride (1.36 g, 6.40 mMol) and the solution stirred overnight. Upon arrival the solution was diluted with ethyl acetate (200 mL). The mixture was washed with saturated sodium bicarbonate solution (75 mL), water (75 mL), and brine (75 mL). The organic layer was then dried with magnesium sulfate, filtered, concentrated, and purified by flash column chromatography on silica gel using 40% ethyl acetate in hexane as the eluant to yield 850 mg (68% yield) of 2-(4-tert-Butyl-phenyl)-4-[4-(3-fluoro-4-nitro-benzyl)-piperazin-1-yl]-1H-benzoimidazole as a light yellow solid. 1H NMR (DMSO-d6): δ=12.69 (s, 1H), 8.16 (t, 1H, J=8.2 Hz), 8.04 (d, 2H, J=8.5 Hz), 7.59 (m, 1H), 7.55 (d, 2H, J=8.5 Hz), 7.47 (d, 1H, J=8.6 Hz), 7.03 (m, 2H), 6.50 (dd, 1H, J=7.0, 1.8 Hz), 3.71 (s, 2H), 3.60 (br s, 4H), 2.66 (br s, 4H), 1.33 (s, 9H). LC/MS (Method A), rt=1.24 mins., purity=100%, calculated mass=487, [M+H]+=488, [M−H]−=486.

후처리

  1. washThe mixture was washed with saturated sodium bicarbonate solution (75 mL), water (75 mL), and brine (75 mL)
  2. dry with materialThe organic layer was then dried with magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by flash column chromatography on silica gel using 40% ethyl acetate in hexane as the eluant

출처 및 근거

ORD 기록
ord-b506f1e2c2f94482a18c0ff4c0e8b3ff
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07696210B2

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