Tetrahydrofuran → 3-Methyl-5-(5-(trifluoromethyl)pyridin-2-yloxy)phenylboronic acid

HRID 1666453노트

반응식

HRID 1666453 반응식
Br[C:2]1[CH:3]=[C:4]([CH:16]=[C:17]([CH3:19])[CH:18]=1)[O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][N:7]=1.C([O:23][B:24](OC(C)C)[O:25]C(C)C)(C)C.C1COCC1.[Li]CCCC>C1(C)C=CC=CC=1>[CH3:19][C:17]1[CH:18]=[C:2]([B:24]([OH:25])[OH:23])[CH:3]=[C:4]([O:5][C:6]2[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][N:7]=2)[CH:16]=1

참가 물질

6

반응물 4

HCID 8028TetrahydrofuranHCID 21531Triisopropyl borateHCID 668769062-(3-Bromo-5-methylphenoxy)-5-(trifluoromethyl)pyridineHCID 178418339Butyllithium

생성물 1

HCID 668762393-Methyl-5-(5-(trifluoromethyl)pyridin-2-yloxy)phenylboronic acid수율 121.2%

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
-40 °C

실험 절차

2-(3-Bromo-5-methylphenoxy)-5-(trifluoromethyl)pyridine (2 g, 0.006 mol) and triisopropylborate (1.66 mL, 0.0072 mol) were dissolved in toluene (40 mL) and THF (20 mL) and cooled to −78° C. n-BuLi (5.38 mL, 0.006 mol) was added while maintaining the reaction at −70° C. The reaction was stirred for 1 h at −40° C. Gradually the temperature was increased to −20-0° C. and the reaction was quenched with 2NHCl. The reaction mixture was warmed to RT, concentrated and extracted with EtOAc. The organic extract was dried over Na2SO4 and concentrated under reduced pressure to give the title compound (2.16 g).

후처리

  1. additionwas added
  2. temperaturewhile maintaining
  3. customthe reaction at −70° C
  4. temperatureGradually the temperature was increased to −20-0° C.
  5. customthe reaction was quenched with 2NHCl
  6. temperatureThe reaction mixture was warmed to RT
  7. concentrationconcentrated
  8. extractionextracted with EtOAc
  9. extractionThe organic extract
  10. dry with materialwas dried over Na2SO4
  11. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-1bdae19e4c0d42208b2cb67c11935435
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08044052B2

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