Potassium Carbonate → HCID 86679135, 화합물

HRID 1774757노트

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HRID 1774757 반응식
[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[N:6][CH:7]=1.C([O-])([O-])=O.[K+].[K+].[C:15]([O:19][C:20]([N:22]1[CH2:25][CH:24](Br)[CH2:23]1)=[O:21])([CH3:18])([CH3:17])[CH3:16].C([O-])(O)=O.[Na+]>CN(C=O)C.CCOC(C)=O>[C:15]([O:19][C:20]([N:22]1[CH2:25][CH:24]([O:8][C:4]2[CH:5]=[N:6][CH:7]=[C:2]([Br:1])[CH:3]=2)[CH2:23]1)=[O:21])([CH3:18])([CH3:16])[CH3:17]

참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 5995293-Bromo-5-hydroxypyridineHCID 53415291tert-Butyl 3-bromoazetidine-1-carboxylate

생성물 1

HCID 86679135HCID 86679135, 화합물수율 100%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매2회HCID 8857Ethyl Acetate용매

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온도
60 °C

실험 절차

To a solution of 5-bromopyridin-3-ol (0.285 g, 1.64 mmol) in DMF (2.5 mL) was added K2CO3 (0.453 g, 3.28 mmol), followed by 3-bromo-azetidine-1-carboxylic acid tert-butyl ester (0.425 g, 1.8 mmol) in DMF (0.5 mL) and the reaction mixture was heated to 60° C. and stirred over night. The reaction mixture was diluted with EtOAc, poured into sat. NaHCO3 solution (10 mL) and the aqueous layer was extracted EtOAc (2×20 mL). Combined organics were washed with brine, dried over Na2SO4, filtered and evaporated to dryness. The residue was purified by silica gel flash chromatography eluting with a 0 to 50% EtOAc-heptane gradient to give the title compound (0.539 g, 100%) as a colorless crystalline solid. MS: 329.1 (M+H+).

후처리

  1. extractionthe aqueous layer was extracted EtOAc (2×20 mL)
  2. washCombined organics were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe residue was purified by silica gel flash chromatography
  7. washeluting with a 0 to 50% EtOAc-heptane gradient

출처 및 근거

ORD 기록
ord-f46151f629f04261814d12a71ad0993b
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09260408B2

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