O-Phenylenediamine → 3-(1H-Benzo[d]imidazol-2-yl)-5-bromo-1H-indazole

HRID 1047523ノート

反応式

HRID 1047523 の反応式
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[C:5]2[CH:11]=O.[C:13]1([NH2:20])[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[NH2:19].S(=O)(O)[O-].[Na+]>C1COCC1.Cl.C(OCC)(=O)C>[NH:19]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:20]=[C:11]1[C:5]1[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([Br:1])[CH:3]=2)[NH:7][N:6]=1

参加物

7

反応物 3

HCID 7243O-PhenylenediamineHCID 23665763Sodium BisulfiteHCID 178520023HCID 178520023、化合物

生成物 1

HCID 1358201453-(1H-Benzo[d]imidazol-2-yl)-5-bromo-1H-indazole収率 50%

試薬・触媒・溶媒 3

HCID 313Hydrochloric Acid触媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

5-Bromo-1H-indazole-3-carbaldehyde (50 mg, 0.222 mmol) and o-phenylene diamine (24 mg, 0.222 mmol) were dissolved in dry THF (10 mL). One drop of 2N HCl was added. The solution was heated at a gentle reflux for 30 min and then 1N sodium bisulfite (1 mL) was added. After overnight at reflux, the solution was cooled to room temperature, and then diluted with ethyl acetate (30 mL). The mixture was washed with water and brine, dried over Na2SO4, and concentrated. Purification by flash chromatography (20% ethyl acetate/hexane) afforded the title compound as a pale yellow solid in a 50% yield. 1H NMR (400 MHz, CDCl3): δ 8.73 (d, 1H, J=1.2 Hz), 7.80 (m, 1H), 7.48-7.45 (m, 2H), 7.37 (d, 1H, J=8.8 Hz), 7.23 (m, 2H); ESI-MS [M+H]+: 313.0.

後処理

  1. temperatureThe solution was heated at
  2. temperaturea gentle reflux for 30 min
  3. temperatureAfter overnight at reflux
  4. washThe mixture was washed with water and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customPurification by flash chromatography (20% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-0a5b981be7474585bf1659ce08bf6ab9
出典データセット
uspto-grants-2013_10
特許番号
US08569511B2

反応ノート

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