Sodium Bicarbonate → HCID 89443836、化合物

HRID 1771715ノート

反応式

HRID 1771715 の反応式
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)[CH:11]=1)[C:6]([OH:8])=O)#[N:2].[NH2:19][C:20]1[C:21]([F:28])=[C:22]([OH:27])[CH:23]=[CH:24][C:25]=1[F:26].C([O-])(O)=O.[Na+]>O=S(Cl)Cl.C1COCC1>[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)[CH:11]=1)[C:6]([NH:19][C:20]1[C:25]([F:26])=[CH:24][CH:23]=[C:22]([OH:27])[C:21]=1[F:28])=[O:8])#[N:2]

参加物

6

反応物 3

HCID 516892Sodium BicarbonateHCID 227559833-Amino-2,4-difluorophenolHCID 89443880HCID 89443880、化合物

生成物 1

HCID 89443836HCID 89443836、化合物収率 67.9%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 24386Thionyl Chloride溶媒

実験手順

3-Cyano-5-(3-fluorophenyl)benzoic acid (500 mg, 2.1 mmol, 1 eq) was dissolved in SOCl2 (15 mL) and heated at reflux overnight. The excess SOCl2 was removed under reduced pressure and the residue that remained dissolved in THF (10 mL) and added dropwise to a mixture of 3-amino-2,4-difluorophenol (280 mg, 2 mmol, 0.95 eq) and NaHCO3 (880 mg, 10.5 mmol, 5 eq) in THF (40 mL). The reaction was stirred at room temperature for 3 h, then filtered and the filtrate concentrated in vacuo. The residue was purified by column chromatography (petroleum ether: EtOAc, 10:1) to give the title compound as a white solid (500 mg, 64%).

後処理

  1. temperatureheated
  2. temperatureat reflux overnight
  3. customThe excess SOCl2 was removed under reduced pressure
  4. dissolutionthe residue that remained dissolved in THF (10 mL)
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated in vacuo
  7. customThe residue was purified by column chromatography (petroleum ether: EtOAc, 10:1)

出典と根拠

ORDレコード
ord-225847c53064427c885b0b44ca8d4496
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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