Ammonium Chloride → HCID 86692510, 화합물

HRID 1748564노트

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HRID 1748564 반응식
[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1)=[O:4].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[Br:21][C:22]1[CH:23]=[C:24]([CH3:29])[C:25](F)=[N:26][CH:27]=1.[Cl-].[NH4+]>C1(C)C=CC=CC=1.O1CCCC1>[CH3:1][O:2][C:3]([C:5]1([C:25]2[C:24]([CH3:29])=[CH:23][C:22]([Br:21])=[CH:27][N:26]=2)[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1)=[O:4]

참가 물질

7

반응물 4

HCID 25517Ammonium ChlorideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 27735202H-Pyran-4-carboxylic acid, tetrahydro-, methyl esterHCID 120569025-Bromo-2-fluoro-3-methylpyridine

생성물 1

HCID 86692510HCID 86692510, 화합물수율 45.5%

시약·촉매·용매 2

HCID 1140Toluene용매2회HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of tetrahydro-2H-pyran-4-carboxylic acid methyl ester (759 mg) in toluene (5 ml) was added dropwise a 1.0 M solution of sodium bis(trimethylsilyl)amide in tetrahydrofuran (5.26 ml) under ice-cooling, and stirred at the same temperature for 1 hour. Then, a solution of 5-bromo-2-fluoro-3-methylpyridine (1 g) in toluene (5 ml) was added dropwise thereto, and stirred at room temperature for 2 hours. After completion of the reaction, a saturated aqueous solution of ammonium chloride was added thereto, and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and then the solvent was evaporated. The obtained residue was purified with silica gel column chromatography (n-hexane/ethyl acetate) to give 4-(5-bromo-3-methylpyridin-2-yl)tetrahydro-2H-pyran-4-carboxylic acid methyl ester (753 mg) as a pale yellow oil. MS (ESI) m/z: 314, 316 (M+H)+.

후처리

  1. temperaturecooling
  2. stirringstirred at room temperature for 2 hours
  3. customAfter completion of the reaction
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. customthe solvent was evaporated
  7. customThe obtained residue was purified with silica gel column chromatography (n-hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-5dba258b31b243f9b7d40b181b6a852d
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09150555B2

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