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

HRID 841537

反応式

HRID 841537 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-fecc842ecb354c87a71827db06611401
出典データセット
uspto-grants-2002_04
特許番号
US06369235B1

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