Sodium hydride → 1H-Benzimidazole, 2-(2,6-difluorophenyl)-1-((2,6-difluorophenyl)methyl)-

HRID 2182080

反応式

HRID 2182080 の反応式
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[NH:10][C:11]2[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=2[N:13]=1.[F:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[C:20]=1[C:26]1C=CC=CC=1CBr.[H-].[Na+]>C1COCC1>[F:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[C:20]=1[CH2:26][N:13]1[C:12]2[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=2[N:10]=[C:9]1[C:3]1[C:4]([F:8])=[CH:5][CH:6]=[CH:7][C:2]=1[F:1]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 16536142-(2,6-difluorophenyl)-1H-benzimidazoleHCID 867579372,6-Difluorophenyl-alpha-bromotoluene

生成物 1

HCID 4688471H-Benzimidazole, 2-(2,6-difluorophenyl)-1-((2,6-difluorophenyl)methyl)-収率 85%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

2-(2,6-difluorophenyl)benzimidazole (Example 12) (2.00 g, 8.70 mmol) and 2,6-difluoro-α-bromo-toluene (25) (2.85 g, 160 M %), were dissolved in THF (20 mL). To this mixture, NaH (0.75 g, 215 M %) was added. After mixing for 2 hours, the reaction was quenched with MeOH and concentrated. The residue was redissolved in ethylacetate, and washed with NaHCO3 (sat. aq.) and NaCl (sat. aq.). The combined washings were dried (Na2SO4), filtered and concentrated. The crude product was recrystallized from ethylacetate/hexane (1:1) yielding white powders of 1-(2,6-difluorobenzyl)-2-(2,6-difluorophenyl)benzimidazole (2.62 g, 0.35 mmol, 85% yield. M.p. 145° C. 1H-NMR (300 MHz, CD2Cl2): δ 7.77 (m, 1H, H4), 7.54 (m, 1H, H4′), 7.49m, 1H, H7), 7.29 (m, 2H, H5,6), 7.24 (m, 1H, H4″), 7.08 (m, 2H, H3′, 5′), 5.82 (m, 2H, H3″, 5″), 5.30 (s, 2H, CH2PhF2).

後処理

  1. additionAfter mixing for 2 hours
  2. customthe reaction was quenched with MeOH
  3. concentrationconcentrated
  4. dissolutionThe residue was redissolved in ethylacetate
  5. washwashed with NaHCO3 (sat. aq.) and NaCl (sat. aq.)
  6. dry with materialThe combined washings were dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product was recrystallized from ethylacetate/hexane (1:1)

出典と根拠

ORDレコード
ord-b472faa513634a938d3b217b1cf168ee
出典データセット
uspto-grants-2005_05
特許番号
US06894068B2

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