Hydrochloric Acid → (5-(Benzyloxy)pyridin-3-yl)boronic acid

HRID 1877476

반응식

HRID 1877476 반응식
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:7]=1.[B:16](OC(C)C)([O:21]C(C)C)[O:17]C(C)C.C([Li])CCC.Cl>C1(C)C=CC=CC=1.O1CCCC1>[CH2:9]([O:8][C:6]1[CH:7]=[C:2]([B:16]([OH:21])[OH:17])[CH:3]=[N:4][CH:5]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 21531Triisopropyl borateHCID 153891983-(Benzyloxy)-5-bromopyridineHCID 178418339Butyllithium

생성물 1

HCID 53398533(5-(Benzyloxy)pyridin-3-yl)boronic acid

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
-70 °C

실험 절차

1.91 g of 3-bromo-5-benzyloxypyridine, under argon, are added to a solution of 2 ml of triisopropyl borate in a mixture of 12 ml of toluene and 3 ml of tetrahydrofuran. The solution is cooled to −70° C. and then 5.42 ml of n-butyllithium (1.6N in hexane) are added dropwise. The reaction medium is stirred for 3 hours, and brought back to −20° C., and 7.23 ml of 2N hydrochloric acid are added dropwise. The reaction mixture is left to return to ambient temperature and poured into distilled water. The aqueous phase is extracted with ethyl acetate, and then the organic phase is washed with a saturated solution of sodium chloride, dried over magnesium sulphate and concentrated under reduced pressure, so as to give 0.21 g of [5-(benzyloxy)pyridin-3-yl]boronic acid in the form of a white powder (adapted from Wenjie Li et al. An Improved Protocol for the Preparation of 3-Pyridyl- and Some Arylboronic Acids J. Org. Chem., (2002), 67(15), 5394-5397), the characteristics of which are the following:

후처리

  1. custombrought back to −20° C.
  2. waitThe reaction mixture is left
  3. customto return to ambient temperature
  4. additionpoured
  5. distillationinto distilled water
  6. extractionThe aqueous phase is extracted with ethyl acetate
  7. washthe organic phase is washed with a saturated solution of sodium chloride
  8. dry with materialdried over magnesium sulphate
  9. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-d601ff0e341248eba784433b0aeaddd8
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08309721B2

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