Potassium Carbonate → (Z)-5-(but-2-en-2-yl)-1-(2-fluoro-4-hydroxyphenyl)-3-methyl-1H-pyrazole-4-carbonitrile

HRID 1410168ノート

反応式

HRID 1410168 の反応式
[F:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:13](I)=[C:12]([C:15]#[N:16])[C:11]([CH3:17])=[N:10]1.[CH3:18]/[C:19](/B(O)O)=[CH:20]/[CH3:21].C([O-])([O-])=O.[K+].[K+]>COCCOC.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:18]/[C:19](/[C:13]1[N:9]([C:3]2[CH:4]=[CH:5][C:6]([OH:8])=[CH:7][C:2]=2[F:1])[N:10]=[C:11]([CH3:17])[C:12]=1[C:15]#[N:16])=[CH:20]/[CH3:21]

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 11389361(E)-But-2-EN-2-ylboronic acidHCID 671200291-(2-fluoro-4-hydroxyphenyl)-5-iodo-3-methyl-1H-pyrazole-4-carbonitrile

生成物 1

HCID 67120037(Z)-5-(but-2-en-2-yl)-1-(2-fluoro-4-hydroxyphenyl)-3-methyl-1H-pyrazole-4-carbonitrile収率 73%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

A mixture of 1-(2-fluoro-4-hydroxyphenyl)-5-iodo-3-methyl-1H-pyrazole-4-carbonitrile (40 mg, 0.12 mmol), (E)-but-2-en-2-ylboronic acid (23.3 mg, 0.23 mmol), K2CO3 (96.7 mg, 0.70 mmol) and Pd(PPh3)4 (13.47 mg, 0.01 mmol) in DME (1 mL) and water (1 mL) was flushed with N2 and irradiated in the microwave at 150° C. for 10 min. Water and DCM were added and the phases were separated. The organic layer was concentrated and the crude product was purified on HPLC to give (Z)-5-(but-2-en-2-yl)-1-(2-fluoro-4-hydroxyphenyl)-3-methyl-1H-pyrazole-4-carbonitrile (23.0 mg, 73%).

後処理

  1. customwas flushed with N2
  2. customirradiated in the microwave at 150° C. for 10 min
  3. additionWater and DCM were added
  4. customthe phases were separated
  5. concentrationThe organic layer was concentrated
  6. customthe crude product was purified on HPLC

出典と根拠

ORDレコード
ord-2cfff2f83352425381cbeb81328e9a01
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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