Potassium Carbonate → 3-[2-(1-t-Butyloxycarbonyl piperidin-4-yloxy)pyridin-5-yl]-1-(morpholin-4-yl)prop-2-ene-1-one

HRID 520815

반응식

HRID 520815 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]([O:8][CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)=[N:6][CH:7]=1.[C:22]([N:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1)(=[O:25])[CH:23]=[CH2:24].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:18]([O:17][C:15]([N:12]1[CH2:13][CH2:14][CH:9]([O:8][C:5]2[CH:4]=[CH:3][C:2]([CH:24]=[CH:23][C:22]([N:26]3[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)=[O:25])=[CH:7][N:6]=2)[CH2:10][CH2:11]1)=[O:16])([CH3:21])([CH3:20])[CH3:19]

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 98723AcryloylmorpholineHCID 21914479tert-Butyl 4-((5-bromopyridin-2-yl)oxy)piperidine-1-carboxylate

생성물 1

HCID 900427223-[2-(1-t-Butyloxycarbonyl piperidin-4-yloxy)pyridin-5-yl]-1-(morpholin-4-yl)prop-2-ene-1-one수율 91.5%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 6228Dimethylformamide용매

실험 절차

A solution of t-butyl 4-(5-bromo pyridin-2-yloxy)piperidine-1-carboxylate (1 gram, 2.80 mmoles), 4-acryloylmorpholine (0.63 gram, 4.46 mmoles), palladium acetate (13 mg, 0.061 mmoles) tri(o-tolyl)phosphine (25.6 mg, 0.084 mmoles) and potassium carbonate (0.62 g, 4.49 mmoles) in DMF (15 mL) was stirred for 3 hours at 140° C. The progress of the reaction was monitored by thin layer chromtography. After completion of reaction, the mass was quenched on to chilled water (30 mL) and the product was extracted with ethyl acetate (3×15 mL). The resulting organic layer was washed with water, dried over sodium sulfate and concentrated under vacuum. The residue, thus obtained, was purified by flash chromatography using ethyl acetate:n-hexane in the ratio of 1:1 to afford the title compound (1.07 grams).

후처리

  1. customAfter completion of reaction
  2. customthe mass was quenched on
  3. temperatureto chilled water (30 mL)
  4. extractionthe product was extracted with ethyl acetate (3×15 mL)
  5. washThe resulting organic layer was washed with water
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under vacuum
  8. customThe residue, thus obtained
  9. customwas purified by flash chromatography

출처 및 근거

ORD 기록
ord-68b517314f804299a5a85ee2f2a0fa9c
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09328092B2

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