Water → HCID 89444094、化合物

HRID 1771737ノート

反応式

HRID 1771737 の反応式
[F:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=2)=[CH:7][C:3]=1[C:4]([OH:6])=O.O=S(Cl)Cl.[NH2:22][C:23]1[C:24]([F:32])=[C:25]([OH:31])[CH:26]=[C:27]([CH3:30])[C:28]=1[F:29].O>C(Cl)Cl.CN(C=O)C.C1COCC1>[F:32][C:24]1[C:25]([OH:31])=[CH:26][C:27]([CH3:30])=[C:28]([F:29])[C:23]=1[NH:22][C:4](=[O:6])[C:3]1[CH:7]=[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=2)[CH:9]=[CH:10][C:2]=1[F:1]

参加物

8

反応物 4

HCID 962WaterHCID 24386Thionyl ChlorideHCID 463123323',4-Difluoro-[1,1'-biphenyl]-3-carboxylic acidHCID 894437823-Amino-2,4-difluoro-5-methylphenol

生成物 1

HCID 89444094HCID 89444094、化合物収率 45%

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide触媒HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of 2-fluoro-5-(3-fluorophenyl)benzoic acid (Intermediate III(a)) (437 mg, 1.87 mmol, 1.1 eq) in CH2Cl2 (10 mL) and DMF (3 drops) was added SOCl2 (15 mL) dropwise at 0° C. The solution was stirred at room temperature for 1 h, then concentrated in vacuo. The residue obtained was dissolved in THF (20 mL) and added dropwise to a solution of 3-amino-2,4-difluoro-5-methyl-phenol (270 mg, 1.70 mmol, 1.0 eq) in THF (10 mL) at 0° C. After addition was completed, the reaction mixture was stirred at room temperature for 2 h, then poured into water and extracted with EtOAc. The combined organic extracts were washed with water and brine, dried (Na2SO4), filtered, and evaporated in vacuo. The residue obtained was purified by column chromatography (petroleum ether: EtOAc, 10:1 to 3:1) to give the title compound as a white solid (285 mg, 45%).

後処理

  1. concentrationconcentrated in vacuo
  2. customThe residue obtained
  3. additionAfter addition
  4. stirringthe reaction mixture was stirred at room temperature for 2 h
  5. extractionextracted with EtOAc
  6. washThe combined organic extracts were washed with water and brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. customevaporated in vacuo
  10. customThe residue obtained
  11. customwas purified by column chromatography (petroleum ether: EtOAc, 10:1 to 3:1)

出典と根拠

ORDレコード
ord-552f183a47ca4dfa8a57912769315f05
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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