N-Methyl-N-(pyridine-2-yl)formamide → 5-(Benzyloxy)-3-bromo-1-methyl-6-oxo-1,6-dihydropyridine-2-carbaldehyde

HRID 625969노트

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HRID 625969 반응식
[CH2:1]([O:8][C:9]1[C:10](=[O:18])[N:11]([CH3:17])[C:12](Br)=[C:13]([Br:15])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Mg]Cl)(C)C.CN(C1C=CC=CN=1)[CH:26]=[O:27]>C1COCC1>[CH2:1]([O:8][C:9]1[C:10](=[O:18])[N:11]([CH3:17])[C:12]([CH:26]=[O:27])=[C:13]([Br:15])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 572611N-Methyl-N-(pyridine-2-yl)formamideHCID 67418185HCID 67418185, 화합물HCID 178418918HCID 178418918, 화합물

생성물 1

HCID 866754905-(Benzyloxy)-3-bromo-1-methyl-6-oxo-1,6-dihydropyridine-2-carbaldehyde수율 84.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
-78 °C

실험 절차

To a −78° C. solution of 3-(benzyloxy)-5,6-dibromo-1-methylpyridin-2(1H)-one (1.5 g, 4.02 mmol) in THF (20 mL) was added 2 M isopropylmagnesium chloride in THF (4.02 mL, 8.04 mmol) dropwise. This mixture was stirred at −78° C. for 15 minutes under nitrogen, and N-methyl-N-pyridin-2-ylformamide (1.4 mL, 12.06 mmol) was added. The mixture was allowed to slowly warm to room temperature overnight. Volatiles were removed under reduced pressure, and the resulting residue was partitioned between dilute aqueous hydrochloric acid and ethyl acetate. The aqueous layer was removed and discarded. The organic layer was collected, dried over anhydrous magnesium sulfate, and purified by silica gel chromatography to afford 5-(benzyloxy)-3-bromo-1-methyl-6-oxo-1,6-dihydropyridine-2-carbaldehyde (1.09 g, 3.38 mmol, 84% yield). ES-MS (M+H)+=323.

후처리

  1. temperatureto slowly warm to room temperature overnight
  2. customVolatiles were removed under reduced pressure
  3. customthe resulting residue was partitioned between dilute aqueous hydrochloric acid and ethyl acetate
  4. customThe aqueous layer was removed
  5. customThe organic layer was collected
  6. dry with materialdried over anhydrous magnesium sulfate
  7. custompurified by silica gel chromatography

출처 및 근거

ORD 기록
ord-975b92a1dad04d289fe25a2fe9fad3de
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309199B2

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