Pyrazole → methyl 6-(1H-pyrazol-1-yl)nicotinate

HRID 720701

반응식

HRID 720701 반응식
[NH:1]1[CH:5]=[CH:4][CH:3]=[N:2]1.[H-].[Na+].Cl[C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][N:10]=1.[NH4+].[Cl-]>CS(C)=O>[CH3:16][O:15][C:13](=[O:14])[C:12]1[CH:17]=[CH:18][C:9]([N:1]2[CH:5]=[CH:4][CH:3]=[N:2]2)=[N:10][CH:11]=1

참가 물질

6

반응물 4

HCID 1048PyrazoleHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 254249Methyl 6-chloropyridine-3-carboxylate

생성물 1

HCID 3741563methyl 6-(1H-pyrazol-1-yl)nicotinate수율 93%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

To a solution of pyrazole (19.4 g, 0.28 mol) in 100 mL anhydrous DMSO, which was at a temperature of 0° C., was added NaH (7.5 g, 0.3 mol) gradually over a period of 30 min. The resulting reaction mixture was allowed to warm to room temperature, at which the mixture continued to agitate for an additional 30 min. Methyl 6-chloronicotinate (35 g, 0.2 mol) was added to the stirring reaction mixture and agitated vigorously for a period of 6 hr. The reaction mixture was subsequently cooled to a temperature of about 0° C. and poured into a saturated aqueous, 0° C. NH4Cl solution. The resulting precipitate was filtered, washed with water, and dried to give a compound of formula (XI-a) (38.3 g, 93% yield) as an off-white solid.

후처리

  1. customwas at a temperature of 0° C.
  2. customThe resulting reaction mixture
  3. stirringagitated vigorously for a period of 6 hr
  4. temperatureThe reaction mixture was subsequently cooled to a temperature of about 0° C.
  5. additionpoured into a saturated aqueous, 0° C
  6. filtrationThe resulting precipitate was filtered
  7. washwashed with water
  8. customdried
  9. customto give a compound of formula (XI-a) (38.3 g, 93% yield) as an off-white solid

출처 및 근거

ORD 기록
ord-0599d0c7b18f4778a3a100508a329676
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07135573B2

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