Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 68585126、化合物

HRID 17507ノート

反応式

HRID 17507 の反応式
[C:1]1([C:6]([O:8][C:9]2[C:10]([F:25])=[C:11]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:12]([CH3:18])=[C:13]([C:16]#[N:17])[C:14]=2[NH2:15])=O)[CH2:5][CH2:4][CH2:3][CH:2]=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C1(C)C(C)=CC=CC=1>[C:1]1([C:6]2[O:8][C:9]3[C:14](=[C:13]([C:16]#[N:17])[C:12]([CH3:18])=[C:11]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[C:10]=3[F:25])[N:15]=2)[CH2:5][CH2:4][CH2:3][CH:2]=1

参加物

4

反応物 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 866308604-Amino-5-cyano-2-fluoro-6-methylbiphenyl-3-yl cyclopentenecarboxylate

生成物 1

HCID 68585126HCID 68585126、化合物収率 87%

試薬・触媒・溶媒 1

HCID 7237O-Xylene溶媒

実験手順

4-Amino-5-cyano-2-fluoro-6-methylbiphenyl-3-yl cyclopentenecarboxylate (I-213) (180 mg, 0.54 mmol) was dissolved in xylene (50 ml), pyridinium p-toluenesulfonate (50 mg) was added, followed by heating under reflux for 5 hours. After cooling to room temperature, the solvent was evaporated away under reduced pressure. The resulting residue was diluted with ethyl acetate, and washed with saturated brine. The obtained organic layer was dried over anhydrous sodium sulfate, the solvent was evaporated away under reduced pressure. The resulting residue was subjected to silica gel column chromatography, and eluted with a mixed solvent of n-hexane/ethyl acetate (4:1, v/v) to obtain the entitled compound (148 mg, 87%) as a white crystal.

後処理

  1. temperatureby heating
  2. temperatureunder reflux for 5 hours
  3. customthe solvent was evaporated away under reduced pressure
  4. additionThe resulting residue was diluted with ethyl acetate
  5. washwashed with saturated brine
  6. dry with materialThe obtained organic layer was dried over anhydrous sodium sulfate
  7. customthe solvent was evaporated away under reduced pressure
  8. washeluted with a mixed solvent of n-hexane/ethyl acetate (4:1

出典と根拠

ORDレコード
ord-cd068948037a46c1a9ace3ee6761f9ff
出典データセット
uspto-grants-2010_06
特許番号
US07737166B2

反応ノート

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