Phosphorus oxychloride → ethyl 4-cyano-6,7-dihydro-1,3-dimethyl-1H-indazole-5-carboxylate

HRID 259725노트

반응식

HRID 259725 반응식
[C:1]([C:3]1(O[Si](C)(C)C)[CH:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:10][CH2:9][C:8]2[N:7]([CH3:17])[N:6]=[C:5]([CH3:18])[C:4]1=2)#[N:2].P(Cl)(Cl)(Cl)=O>N1C=CC=CC=1>[C:1]([C:3]1[C:4]2[C:5]([CH3:18])=[N:6][N:7]([CH3:17])[C:8]=2[CH2:9][CH2:10][C:11]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13])#[N:2]

참가 물질

4

반응물 2

HCID 24813Phosphorus oxychlorideHCID 22402969ethyl 4-cyano-4,5,6,7-tetrahydro-1,3-dimethyl-4-(trimethylsilyloxy)-1H-indazole-5-carboxylate

생성물 1

HCID 22402928ethyl 4-cyano-6,7-dihydro-1,3-dimethyl-1H-indazole-5-carboxylate수율 53.1%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

A solution of ethyl 4-cyano-4,5,6,7-tetrahydro-1,3-dimethyl-4-(trimethylsilyloxy)-1H-indazole-5-carboxylate (28.1 g, 0.119 mol) in pyridine is mixed with phosphorus oxychloride (43.0 mL, 0.461 mol), stirred for 5 hours at reflux temperature and concentrated in vacuo. The resultant black residue is diluted with ethyl acetate and water and treated with sodium bicarbonate to pH 6. The phases are separated, the organic phase is set aside, and the aqueous phase is extracted with ethyl acetate. The organic phases are combined, washed with aqueous sodium bicarbonate and water, dried (MgSO4) and concentrated in vacuo to give a black residue. The residue is triturated under ethyl acetate to give the title product as a tan solid (15.5 g, 52.9%), identified by 1HNMR and IR spectroscopy.

후처리

  1. temperatureat reflux temperature
  2. concentrationconcentrated in vacuo
  3. additionThe resultant black residue is diluted with ethyl acetate and water
  4. additiontreated with sodium bicarbonate to pH 6
  5. customThe phases are separated
  6. extractionthe aqueous phase is extracted with ethyl acetate
  7. washwashed with aqueous sodium bicarbonate and water
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated in vacuo
  10. customto give a black residue
  11. customThe residue is triturated under ethyl acetate

출처 및 근거

ORD 기록
ord-ece7347a52ba428c97e8ebd5c1a0f7f2
출처 데이터셋
uspto-grants-1996_06
특허 번호
US05523279

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