Ammonium Chloride → 3-((7-Chloropyrazolo[1,5-a]pyrimidin-5-yl)methyl)benzonitrile

HRID 624742ノート

反応式

HRID 624742 の反応式
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]2[N:9]=[CH:10][CH:11]=[C:4]2[N:3]=1.[Br-].[C:13]([C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH2:18][Zn+])#[N:14].[NH4+].[Cl-]>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.CN(C=O)C>[Cl:8][C:6]1[N:5]2[N:9]=[CH:10][CH:11]=[C:4]2[N:3]=[C:2]([CH2:18][C:17]2[CH:16]=[C:15]([CH:22]=[CH:21][CH:20]=2)[C:13]#[N:14])[CH:7]=1

参加物

6

反応物 3

HCID 25517Ammonium ChlorideHCID 110741545,7-Dichloropyrazolo[1,5-a]pyrimidineHCID 178509756HCID 178509756、化合物

生成物 1

HCID 866546533-((7-Chloropyrazolo[1,5-a]pyrimidin-5-yl)methyl)benzonitrile収率 64%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

To the reaction flask, 5,7-dichloropyrazolo[1,5-a]pyrimidine (452 mg, 2.4 mmol) was added along with (3-cyanobenzyl)zinc(II) bromide (6 mL, 3.75 mmol, 0.625M in DMF), Pd(PPh3)4 (110 mg, 0.1 mmol), and DMF (10 mL). The reaction was heated at 60° C. for 4 hours then cooled to room temperature. The reaction mixture was poured into saturated aqueous NH4Cl solution and ice and extracted with ethyl acetate. The combined extracts were washed with water, saturated NaCl solution, and then dried over Na2SO4. The solvent was removed in vacuo and the residue was purified by column chromatography on silica using 35% ethyl acetate/hexanes as the eluent. The product, 3-((7-chloropyrazolo[1,5-a]pyrimidin-5-yl)methyl)benzonitrile, was recovered in 64% yield. LCMS (M+1=269)

後処理

  1. temperaturethen cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe combined extracts were washed with water, saturated NaCl solution
  4. dry with materialdried over Na2SO4
  5. customThe solvent was removed in vacuo
  6. customthe residue was purified by column chromatography on silica using 35% ethyl acetate/hexanes as the eluent
  7. customThe product, 3-((7-chloropyrazolo[1,5-a]pyrimidin-5-yl)methyl)benzonitrile, was recovered in 64% yield

出典と根拠

ORDレコード
ord-9e138917faa74b6a9fb651f55b5785bb
出典データセット
uspto-grants-2016_04
特許番号
US09303033B2

反応ノート

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