Sodium hydride → 1-(2,6-Difluorobenzyl)-2-(2-Fluoro-6-Methoxylphenyl)-4-Nitrobenzimidazole

HRID 841537

반응식

HRID 841537 반응식
[F:1][C:2]1[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[C:3]=1[CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[C:13]([N+:14]([O-:16])=[O:15])[C:8]=2[N:7]=[C:6]1[C:17]1[C:22](F)=[CH:21][CH:20]=[CH:19][C:18]=1[F:24].FC1C=CC=C(F)C=1CBr.[H-].[Na+].[CH2:42]([O:44]C(=O)C)C.CCCCCC>C1COCC1>[F:1][C:2]1[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[C:3]=1[CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[C:13]([N+:14]([O-:16])=[O:15])[C:8]=2[N:7]=[C:6]1[C:17]1[C:22]([O:44][CH3:42])=[CH:21][CH:20]=[CH:19][C:18]=1[F:24]

참가 물질

6

반응물 4

HCID 24758Sodium hydrideHCID 4926701-(2,6-Difluorobenzyl)-2-(2,6-difluorophenyl)-4-nitrobenzimidazoleHCID 5814352-(Bromomethyl)-1,3-difluorobenzeneHCID 21226206Ethyl acetate hexane

생성물 1

HCID 224824531-(2,6-Difluorobenzyl)-2-(2-Fluoro-6-Methoxylphenyl)-4-Nitrobenzimidazole

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To 1-(2,6-difluorobenzyl)-2-(2,6-difluorophenyl)-4-nitrobenzimidazole (2.00 g, 8 mmol)was added 2,6-difluorobenzylbromide (2.0.2 g, 9.76 mmol, 130 M%) dissolved in THF (20 mL) was added NaH (0.84 g, 21 mmol, 290 M%). After 8 h, the reaction was quenched with m ethanol and concentrated. The residue was dissolved in CH2Cl2, and washed with water and NaCl (sat. aq.). The combined washings were dried (Na2SO4), filtered, concentrated. The crude product was purified by flash chromatography eluting with ethylacetate:hexane (1:1) (2.33 g, 5.64 mmol, 78%). M.p. 189-192° C. 1H-NMR (200 MHz, CD2Cl2) δ8.11 (dd, J=8.1, 1.0 Hz, 1H, H5), 7.84 (dd, J=8.1, 1.0 Hz, 1H, H7), 7.52 (m, 1H, H4′), 7.40 (dd, J=8.1 Hz, 1H, H6), 7.26 (m, 1H, H4″), 6.89-6.74 (m, 4H, H3′,5′,35″,5″), 5.36 (d, J=3.4 Hz, 2H, CH2PhF2 (rotamers)), 3.73 (s, 3H, OCH3).

후처리

  1. customthe reaction was quenched with m ethanol
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in CH2Cl2
  4. washwashed with water and NaCl (sat. aq.)
  5. dry with materialThe combined washings were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by flash chromatography

출처 및 근거

ORD 기록
ord-fecc842ecb354c87a71827db06611401
출처 데이터셋
uspto-grants-2002_04
특허 번호
US06369235B1

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