Cesium carbonate → HCID 87730327、化合物

HRID 1392269ノート

反応式

HRID 1392269 の反応式
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10]Br)=[CH:6][C:5]=1[Br:12].[CH2:14]([N:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23]([CH:30]=[N:31][OH:32])=[CH:22]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CC(C)=O>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][O:32]/[N:31]=[CH:30]/[C:23]2[C:24]3[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=3)[N:21]([CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:22]=2)=[CH:6][C:5]=1[Br:12]

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 46376791-Benzyl-1H-indole-3-carbaldehyde oximeHCID 19806367Methyl 2-bromo-4-(bromomethyl)benzoate

生成物 1

HCID 87730327HCID 87730327、化合物収率 34%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

To a solution of 2-bromo-4-bromomethyl-benzoic acid methyl ester (0.50g, 1.62 mmol) and 1-benzyl-1H-indole-3-carbaldehyde oxime (0.43 g, 1.70 mmol) in acetone (50 mL) was added cesium carbonate (2.12 g, 6.49 mmol). The mixture was heated to reflux for 6 hours and allowed to cool back to room temperature. The mixture was partitioned between ethyl acetate and brine and the layers were then separated. The aqueous layer was extracted with one additional portion of ethyl acetate. The organics were combined, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The crude material was purified by flash chromatography through silica gel using ethyl acetate/hexanes (0/100 gradient to 20/80) to give an off-white solid. This solid was recrystallized one time from ethyl acetate/hexanes (1/6) to give 4-[({[(1E)-(1-benzyl-1H-indol-3-yl)methylidene]amino}oxy)methyl]-2-bromobenzoic acid methyl ester (0.26 g, 34%) as off-white crystals. 1H NMR (400 MHz, CDCl3); δ 8.12 (s, 1H), 7.76 (m, 4H), 7.68 (s, 1H), 7.35 (d, 1H), 7.28 (m, 3H), 7.23 (m, 2H), 7.11 (d, 2H), 5.33 (s, 2H), 5.27 (s, 2H), 3.90 (s, 3H).

後処理

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 6 hours
  3. customThe mixture was partitioned between ethyl acetate and brine
  4. customthe layers were then separated
  5. extractionThe aqueous layer was extracted with one additional portion of ethyl acetate
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe crude material was purified by flash chromatography through silica gel
  10. customto give an off-white solid
  11. customThis solid was recrystallized one time from ethyl acetate/hexanes (1/6)

出典と根拠

ORDレコード
ord-6744f371effa45a6b96ba97603337f62
出典データセット
uspto-grants-2008_03
特許番号
US07342039B2

反応ノート

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