Sodium hydride → Methyl 5-chloro-6-[(1,3-difluoropropan-2-yl)oxy]nicotinate

HRID 217468

반응식

HRID 217468 반응식
[Cl:1][C:2]1[C:3](Cl)=[N:4][CH:5]=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[H-].[Na+].[F:15][CH2:16][CH:17]([OH:20])[CH2:18][F:19]>C1COCC1>[Cl:1][C:2]1[C:3]([O:20][CH:17]([CH2:18][F:19])[CH2:16][F:15])=[N:4][CH:5]=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 679851,3-Difluoro-2-propanolHCID 2782166Methyl 5,6-Dichloronicotinate

생성물 1

HCID 67363966Methyl 5-chloro-6-[(1,3-difluoropropan-2-yl)oxy]nicotinate수율 80.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

Methyl 5,6-dichloronicotinate (1.5 g) and 60% sodium hydride (640 mg) were dissolved in THF (45 mL). 1,3-Difluoropropan-2-ol (1.5 g) was added thereto at 0° C., followed by stirring at 0° C. for 3 hours, and the reaction solution was quenched with aqueous NH4Cl. After extraction with EtOAc, the organic layer was dried over MgSO4 and then filtered, and the desiccant was removed. The vehicle was evaporated under reduced pressure, followed by purification by silica gel column chromatography (hexane:AcOEt=100:0 to 50:50) to obtain methyl 5-chloro-6-[(1,3-difluoropropan-2-yl)oxy]nicotinate (1.56 g) as a colorless liquid.

후처리

  1. customat 0° C.
  2. customthe reaction solution was quenched with aqueous NH4Cl
  3. extractionAfter extraction with EtOAc
  4. dry with materialthe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. customthe desiccant was removed
  7. customThe vehicle was evaporated under reduced pressure
  8. customfollowed by purification by silica gel column chromatography (hexane:AcOEt=100:0 to 50:50)

출처 및 근거

ORD 기록
ord-6d3346eb5732435ab3e1c1b3e3aff310
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08193378B2

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