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

HRID 242193ノート

反応式

HRID 242193 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-ee113c1f054b4bb19a92df2010d44390
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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