Acetonitrile → HCID 90418212、化合物

HRID 923692ノート

反応式

HRID 923692 の反応式
[NH2:1][C:2]1[C:7]([F:8])=[C:6](Br)[N:5]=[C:4]([C:10]([O:12][CH3:13])=[O:11])[C:3]=1[Cl:14].[S:15]1[C:19]2[CH:20]=[CH:21][C:22](B(O)O)=[CH:23][C:18]=2[N:17]=[CH:16]1.[F-].[K+].CC#N>ClCCl.CC([O-])=O.CC([O-])=O.[Pd+2].O>[NH2:1][C:2]1[C:7]([F:8])=[C:6]([C:22]2[CH:21]=[CH:20][C:19]3[S:15][CH:16]=[N:17][C:18]=3[CH:23]=2)[N:5]=[C:4]([C:10]([O:12][CH3:13])=[O:11])[C:3]=1[Cl:14]

参加物

8

反応物 4

HCID 6342AcetonitrileHCID 522689Potassium FluorideHCID 18452959HCID 18452959、化合物HCID 71551894Methyl 4-amino-6-bromo-3-chloro-5-fluoropicolinate

生成物 1

HCID 90418212HCID 90418212、化合物収率 51%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
150 °C

実験手順

To a 5 mL microwave vial was added methyl 4-amino-6-bromo-3-chloro-5-fluoropicolinate (200 mg, 1.0 mmol), benzo[d]thiazol-5-ylboronic acid (237 mg, 1.35 mmol), potassium fluoride (KF; 122 mg, 2.12 mmol), TPPTS-Na (tris-(3-sulfornatophenyl)-phosphine4-hydrate sodium salt, 67 mg, 0.106 mmol) and Pd(OAc)2 (11 mg, 0.053 mmol). Subsequently, CH3CN (1.0 mL) and H2O (3.0 mL) were added, and the reaction vial was sealed and heated in a Biotage microwave at 150° C. for 5 min, with external IR-sensor temperature monitoring from the side of the vessel. The reaction mixture was cooled to room temperature and diluted with dicloromethane, and washed wth water. The organic extracts were combined, dried (Na2SO4), filtered, and concentrated in vacuo. The crude product was purified by triturating with Et2O to yield the title compound as a brown solid (172 mg, 51%).

後処理

  1. customthe reaction
  2. customvial was sealed
  3. temperatureThe reaction mixture was cooled to room temperature
  4. washwashed wth water
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified
  9. customby triturating with Et2O

出典と根拠

ORDレコード
ord-dafc6c759c97436dba1f3cf3e64c8984
出典データセット
uspto-grants-2016_03
特許番号
US09278985B2

反応ノート

読み込み中…