Triethylamine → 5-Bromo-2-(3,6-dihydro-2H-pyran-4-yl)-3-methylpyridine

HRID 1748563노트

반응식

HRID 1748563 반응식
[Br:1][C:2]1[CH:3]=[C:4]([CH3:15])[C:5]([C:8]2(O)[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[N:6][CH:7]=1.C(N(CC)CC)C.Cl.CN(C)C.S(Cl)(C)(=O)=O>C1(C)C=CC=CC=1.O>[Br:1][C:2]1[CH:3]=[C:4]([CH3:15])[C:5]([C:8]2[CH2:13][CH2:12][O:11][CH2:10][CH:9]=2)=[N:6][CH:7]=1

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 10313079Trimethylamine HydrochlorideHCID 866925094-(5-Bromo-3-methylpyridin-2-yl)-tetrahydro-2H-pyran-4-ol

생성물 1

HCID 866925085-Bromo-2-(3,6-dihydro-2H-pyran-4-yl)-3-methylpyridine수율 86.8%

시약·촉매·용매 2

HCID 962Water용매HCID 1140Toluene용매

실험 절차

4-(5-Bromo-3-methylpyridin-2-yl)-tetrahydro-2H-pyran-4-ol (2.95 g), triethylamine (3 ml) and trimethylamine monohydrochloride (103 mg) were suspended in toluene (50 ml), mesyl chloride (1.26 ml) was added thereto under ice-cooling, then warmed to room temperature, and stirred for 72 hours. After completion of the reaction, water was added thereto, extracted with chloroform, the organic layer was dried over anhydrous sodium sulfate, and then the solvent was evaporated in vacuo. The obtained residue was purified with silica gel column chromatography (n-hexane/ethyl acetate) to give the titled compound (2.39 g) as a white solid. MS (ESI) m/z: 254, 256 (M+H)+.

후처리

  1. temperatureunder ice-cooling
  2. additionwas added
  3. extractionextracted with chloroform
  4. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated in vacuo
  6. customThe obtained residue was purified with silica gel column chromatography (n-hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-710ad3062e7844aeb020b8259f2007b3
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09150555B2

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