HCID 89443836、化合物 → HCID 89443808、化合物

HRID 1771716ノート

反応式

HRID 1771716 の反応式
[C:1]([C:3]1[CH:4]=[C:5]([CH:18]=[C:19]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=2)[CH:20]=1)[C:6]([NH:8][C:9]1[C:14]([F:15])=[CH:13][CH:12]=[C:11]([OH:16])[C:10]=1[F:17])=O)#[N:2]>C1COCC1>[F:17][C:10]1[C:11]([OH:16])=[CH:12][CH:13]=[C:14]([F:15])[C:9]=1[NH:8][CH2:6][C:5]1[CH:4]=[C:3]([CH:20]=[C:19]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=2)[CH:18]=1)[C:1]#[N:2]

参加物

3

反応物 1

HCID 89443836HCID 89443836、化合物

生成物 1

HCID 89443808HCID 89443808、化合物収率 29,267.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
50 °C

実験手順

To a solution of 3-Cyano-N-(2,6-difluoro-3-hydroxy-phenyl)-5-(3-fluorophenyl)benzamide (500 mg, 2.7 mmol, 1.0 eq) in THF (30 mL) at 0° C. was added a solution of BH3 (1M in THF, 10.8 mL, 10.8 mmol, 4.0 eq) dropwise. The reaction was then heated at 50° C. for 6 h. The reaction was cooled to room temperature and quenched by addition of aqueous NH4Cl. The aqueous layer was extracted with EtOAc and the combined organic extracts dried (Na2SO4), filtered and evaporated in vacuo. The residue obtained was purified by column chromatography (petroleum ether:EtOAc, 7:1) to give the title compound as white solid (280 g, 58%).

後処理

  1. temperatureThe reaction was cooled to room temperature
  2. customquenched by addition of aqueous NH4Cl
  3. extractionThe aqueous layer was extracted with EtOAc
  4. dry with materialthe combined organic extracts dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe residue obtained
  8. customwas purified by column chromatography (petroleum ether:EtOAc, 7:1)

出典と根拠

ORDレコード
ord-053f1ee0463045d29516fbcc35fca811
出典データセット
uspto-grants-2016_02
特許番号
US09249085B2

反応ノート

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