[6-(4-Bromo-2-chloro-phenylamino)-7-fluoro-3H-benzoimidazol-5-yl]-methanol → 6-(4-Bromo-2-chloro-phenylamino)-7-fluoro-3H-benzoimidazole-5-carbaldehyde

HRID 216470ノート

反応式

HRID 216470 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:10]([CH2:19][OH:20])=[CH:11][C:12]3[NH:16][CH:15]=[N:14][C:13]=3[C:17]=2[F:18])=[C:4]([Cl:21])[CH:3]=1>O1CCCC1.CC(C)=O.O=[Mn]=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:10]([CH:19]=[O:20])=[CH:11][C:12]3[NH:16][CH:15]=[N:14][C:13]=3[C:17]=2[F:18])=[C:4]([Cl:21])[CH:3]=1

参加物

4

反応物 1

HCID 11428680[6-(4-Bromo-2-chloro-phenylamino)-7-fluoro-3H-benzoimidazol-5-yl]-methanol

生成物 1

HCID 112456086-(4-Bromo-2-chloro-phenylamino)-7-fluoro-3H-benzoimidazole-5-carbaldehyde収率 85.2%

試薬・触媒・溶媒 2

HCID 14801Manganese dioxide触媒HCID 22559816Acetone tetrahydrofuran溶媒

反応条件

温度
50 °C

実験手順

[6-(4-Bromo-2-chloro-phenylamino)-7-fluoro-3H-benzoimidazol-5-yl]-methanol 10e (0.96 g, 2.58 mmol) is dissolved in tetrahydrofuran/acetone (1:1, 15 mL), and MnO2 (2.24 g, 25.8 mmol) is added. The reaction mixture is stirred at 50° C. for 10 hours under N2. The reaction mixture is filtered through silica gel and eluted with methylene chloride/methanol (10:1, 1 L). The filtrate is concentrated under reduced pressure to a small volume and then filtered through an Acrodisc syringe filter to remove small amounts of MnO2 that passed through the silica gel. The filtrate is concentrated under reduced pressure and the residue is purified by flash column chromatography (eluting with 20:1 methylene chloride:methanol) to yield 0.81 g (85%) of the pure desired product as a bright yellow solid. MS ESI (+) m/z 368, 370 (M+, Br pattern) detected.

後処理

  1. filtrationThe reaction mixture is filtered through silica gel
  2. washeluted with methylene chloride/methanol (10:1, 1 L)
  3. concentrationThe filtrate is concentrated under reduced pressure to a small volume
  4. filtrationfiltered through an Acrodisc syringe
  5. filtrationfilter
  6. customto remove small amounts of MnO2 that
  7. concentrationThe filtrate is concentrated under reduced pressure
  8. customthe residue is purified by flash column chromatography (eluting with 20:1 methylene chloride:methanol)

出典と根拠

ORDレコード
ord-bafce661e30244d0b1c663acf6294f94
出典データセット
uspto-grants-2012_06
特許番号
US08193229B2

反応ノート

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