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

HRID 1927976노트

반응식

HRID 1927976 반응식
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

참가 물질

6

반응물 4

HCID 5234Sodium ChlorideHCID 21531Triisopropyl borate2회HCID 574687452-(3-Bromo-phenyl)-6-methyl-4-(4-trifluoromethyl-phenyl)-pyridineHCID 178418339Butyllithium2회

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.).

후처리

  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

출처 및 근거

ORD 기록
ord-2b05f3767eab41e9b95da984639bfa62
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08183262B2

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