2,5-Hexanedione → 5-(2,5-dimethyl-1H-pyrrol-1-yl)-1-(2-fluoro-4-hydroxyphenyl)-3-methyl-1H-pyrazole-4-carbonitrile

HRID 1410142ノート

反応式

HRID 1410142 の反応式
[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][C:8]=2[F:14])[N:5]=[C:4]([CH3:15])[C:3]=1[C:16]#[N:17].[CH2:18]([CH2:22][C:23](=O)[CH3:24])[C:19]([CH3:21])=O.CCOC(C)=O>CC(OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=O>[CH3:24][C:23]1[N:1]([C:2]2[N:6]([C:7]3[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][C:8]=3[F:14])[N:5]=[C:4]([CH3:15])[C:3]=2[C:16]#[N:17])[C:19]([CH3:21])=[CH:18][CH:22]=1

参加物

5

反応物 3

HCID 80352,5-HexanedioneHCID 8857Ethyl AcetateHCID 671200435-amino-1-(2-fluoro-4-hydroxyphenyl)-3-methyl-1H-pyrazole-4-carbonitrile

生成物 1

HCID 671200565-(2,5-dimethyl-1H-pyrrol-1-yl)-1-(2-fluoro-4-hydroxyphenyl)-3-methyl-1H-pyrazole-4-carbonitrile収率 99%

試薬・触媒・溶媒 1

HCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl ester溶媒

実験手順

A solution of 5-amino-1-(2-fluoro-4-hydroxyphenyl)-3-methyl-1H-pyrazole-4-carbonitrile (100 mg, 0.43 mmol) and acetonylacetone (507 μL, 4.31 mmol) in glacial acetic (3 mL) acid was heated at 140° C. in the micro for 30 min. The mixture was transferred to a round bottom flask using EtOAc and evaporated, toluene was added and again evaporated, CH2Cl2 and silica was finally added and the mixture was evaporated to dryness. Purification using silica chromatography (short plug) gave 5-(2,5-dimethyl-1H-pyrrol-1-yl)-1-(2-fluoro-4-hydroxyphenyl)-3-methyl-1H-pyrazole-4-carbonitrile (132 mg, 99%) as a 1:1 mixture with the starting material acetonylacetone. The product was used as such in the next step.

後処理

  1. customThe mixture was transferred to a round bottom flask
  2. customevaporated
  3. additiontoluene was added
  4. customagain evaporated
  5. additionCH2Cl2 and silica was finally added
  6. customthe mixture was evaporated to dryness
  7. customPurification

出典と根拠

ORDレコード
ord-71d2716fbff548d7bd3f2d3d136539f8
出典データセット
uspto-grants-2014_12
特許番号
US08921402B2

反応ノート

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