Sodium Chloride → 3-[6-Methyl-4-(4-trifluoromethyl-phenyl)pyridin-2-yl]-benzeneboronic acid

HRID 1927976ノート

反応式

HRID 1927976 の反応式
Br[C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=3)[CH:11]=[C:10]([CH3:24])[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[B:25](OC(C)C)([O:30]C(C)C)[O:26]C(C)C.[Li]CCCC.[Na+].[Cl-]>C1COCC1>[CH3:24][C:10]1[N:9]=[C:8]([C:4]2[CH:3]=[C:2]([B:25]([OH:30])[OH:26])[CH:7]=[CH:6][CH:5]=2)[CH:13]=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=2)[CH:11]=1

参加物

6

反応物 4

HCID 5234Sodium ChlorideHCID 21531Triisopropyl borate2 回HCID 574687452-(3-Bromo-phenyl)-6-methyl-4-(4-trifluoromethyl-phenyl)-pyridineHCID 178418339Butyllithium2 回

生成物 1

HCID 602093413-[6-Methyl-4-(4-trifluoromethyl-phenyl)pyridin-2-yl]-benzeneboronic acid収率 120.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 2-(3-bromo-phenyl)-6-methyl-4-(4-trifluoromethyl-phenyl)-pyridine (example E.21) (4.00 g, 10.2 mmol) and triisopropyl borate (2.23 g, 11.8 mmol) in THF (60 mL) at −78° C. was added n-BuLi (1.6 M in hexane, 6.50 mL, 10.4 mmol) keeping the internal temperature below −65° C. Stirring was continued at −78° C. for 45 min, again triisopropyl borate (1.11 g, 5.9 mmol) and n-BuLi (1.6 M in hexane, 3.25 mL, 5.2 mmol) were added and stirring was continued at −78° C. for 30 min. A 1 M aqueous solution of NaH2PO4.2H2O was added, saturated with solid NaCl and extracted with EtOAc. The organic layer was dried over Na2SO4, filtered and the solvent was removed in vacuum to give the title compound as a yellow solid (4.39 g, 96%). MS (ISP) 358.2 [(M+H)+]; mp 140° C. (dec.).

後処理

  1. customthe internal temperature below −65° C
  2. stirringstirring
  3. waitwas continued at −78° C. for 30 min
  4. extractionextracted with EtOAc
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. customthe solvent was removed in vacuum

出典と根拠

ORDレコード
ord-2b05f3767eab41e9b95da984639bfa62
出典データセット
uspto-grants-2012_05
特許番号
US08183262B2

反応ノート

読み込み中…