Dimethyl Sulfide → (2,4-dimethylthiophen-3-yl)-3-(2-fluoro-4-hydroxyphenyl)-1-methyl-1H-pyrazole-5-carbonitrile

HRID 242225ノート

反応式

HRID 242225 の反応式
[CH3:1][C:2]1[S:3][CH:4]=[C:5]([CH3:24])[C:6]=1[C:7]1[C:8]([C:15]2[CH:20]=[CH:19][C:18]([O:21]C)=[CH:17][C:16]=2[F:23])=[N:9][N:10]([CH3:14])[C:11]=1[C:12]#[N:13].S(C)C>C(Cl)Cl.B(F)(F)F>[CH3:1][C:2]1[S:3][CH:4]=[C:5]([CH3:24])[C:6]=1[C:7]1[C:8]([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][C:16]=2[F:23])=[N:9][N:10]([CH3:14])[C:11]=1[C:12]#[N:13]

参加物

5

反応物 2

HCID 1068Dimethyl SulfideHCID 671200444-(2,4-dimethylthiophen-3-yl)-3-(2-fluoro-4-methoxyphenyl)-1-methyl-1H-pyrazole-5-carbonitrile

生成物 1

HCID 136350247(2,4-dimethylthiophen-3-yl)-3-(2-fluoro-4-hydroxyphenyl)-1-methyl-1H-pyrazole-5-carbonitrile収率 43%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 6356Boron trifluoride溶媒

実験手順

4-(2,4-dimethylthiophen-3-yl)-3-(2-fluoro-4-methoxyphenyl)-1-methyl-1H-pyrazole-5-carbonitrile (17 mg, 0.05 mmol) was dissolved in dry DCM (2 mL) and BF3.Me2S (1 M solution in DCM, 0.3 mL, 0.3 mmol) was added and the mixture was stirred at room temperature over night. The mixture was concentrated and MeOH was added to quench the reaction The crude product was purified on silica gel to give -(2,4-dimethylthiophen-3-yl)-3-(2-fluoro-4-hydroxyphenyl)-1-methyl-1H-pyrazole-5-carbonitrile (7.0 mg, 43%).

後処理

  1. concentrationThe mixture was concentrated
  2. additionMeOH was added
  3. customto quench
  4. customthe reaction The crude product
  5. customwas purified on silica gel

出典と根拠

ORDレコード
ord-d4c76ba032c242fa8baf988ccbaca9d9
出典データセット
uspto-grants-2014_02
特許番号
US08653112B2

反応ノート

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