Triethylamine → 5-(4-Chloro-phenyl)-7-trifluoromethyl-3-trimethylsilanylethynyl-pyrazolo[1,5-a]pyrimidine

HRID 558550ノート

反応式

HRID 558550 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[N:11]3[N:18]=[CH:19][C:20](I)=[C:10]3[N:9]=2)=[CH:4][CH:3]=1.[CH3:22][Si:23]([C:26]#[CH:27])([CH3:25])[CH3:24].CCN(CC)CC>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[N:11]3[N:18]=[CH:19][C:20]([C:27]#[C:26][Si:23]([CH3:25])([CH3:24])[CH3:22])=[C:10]3[N:9]=2)=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 670008255-(4-Chloro-phenyl)-3-iodo-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine

生成物 1

HCID 670009455-(4-Chloro-phenyl)-7-trifluoromethyl-3-trimethylsilanylethynyl-pyrazolo[1,5-a]pyrimidine

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
23 °C

実験手順

A mixture of 5-(4-chloro-phenyl)-3-iodo-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine (example C.4 step 2a and 2b) (13.96 g, 32.96 mmol), trimethylsilylacetylene (5.5 mL, 39.72 mmol) and Et3N (9.2 mL, 67.9 mmol) in dry DMF (33 mL) was stirred for 10 min at 23° C. while being purged with Argon, then PdCl2(PPh3)2 (116 mg, 0.5 mol %), PPh3 (43 mg, 0.5 mol %) and CuI (19 mg, 0.3 mol %) were added. Stirring was continued at 90° C. for 4 h. The react mixture was then cooled to 23° C., diluted with EtOAc, washed water (twice) and brine, dried over Na2SO4. Removal of the solvent left an orange solid (13.30 g, 102%). MS (ISP) 394.1 [(M+H)+] and 396.1 [(M+2+H)+]; mp 198° C.

後処理

  1. customwhile being purged with Argon
  2. additionPdCl2(PPh3)2 (116 mg, 0.5 mol %), PPh3 (43 mg, 0.5 mol %) and CuI (19 mg, 0.3 mol %) were added
  3. stirringStirring
  4. waitwas continued at 90° C. for 4 h
  5. temperatureThe react mixture was then cooled to 23° C.
  6. additiondiluted with EtOAc
  7. washwashed water (twice) and brine
  8. dry with materialdried over Na2SO4
  9. customRemoval of the solvent
  10. waitleft an orange solid (13.30 g, 102%)

出典と根拠

ORDレコード
ord-20567d573b6447b09a7dfdc20d60b760
出典データセット
uspto-grants-2011_11
特許番号
US08063048B2

反応ノート

読み込み中…