Methanol → 6-(Dimethylamino)pyridine-3-boronic acid

HRID 57528

반응식

HRID 57528 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]([N:8]([CH3:10])[CH3:9])=[N:6][CH:7]=1.[Li]CCCC.[B:16](OC(C)C)([O:21]C(C)C)[O:17]C(C)C.CO>C1COCC1>[CH3:9][N:8]([CH3:10])[C:5]1[N:6]=[CH:7][C:2]([B:16]([OH:21])[OH:17])=[CH:3][CH:4]=1

참가 물질

6

반응물 4

HCID 887MethanolHCID 21531Triisopropyl borateHCID 38030415-bromo-N,N-dimethylpyridin-2-amineHCID 178418339Butyllithium

생성물 1

HCID 27632716-(Dimethylamino)pyridine-3-boronic acid

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-72 °C

실험 절차

A solution of 5-bromo-N,N-dimethylpyridin-2-amine (500 mg, 2.5 mmol) in THF (10 mL) was treated with n-BuLi (1.2 mL, 3 mmol) at −72° C. for 2 hours. Triisopropyl borate (705 mg, 3.75 mmol) was then added dropwise. After the completion of the addition, the mixture was stirred at −72° C. for an additional 1 hour and slowly warmed up and stirred at the ambient temperature overnight. MeOH was carefully added, and the volatiles were removed under reduced pressure to give the title compound. MS (m/z): 167 (M+H)+.

후처리

  1. additionAfter the completion of the addition
  2. temperatureslowly warmed up
  3. stirringstirred at the ambient temperature overnight
  4. customthe volatiles were removed under reduced pressure

출처 및 근거

ORD 기록
ord-1d1e0032d13f4159b2fc306ea574db4d
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434726B2

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