Dimethyl Sulfoxide → methyl 1-(2-oxoethyl)-1H-indazole-7-carboxylate

HRID 2168495노트

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HRID 2168495 반응식
CS(C)=O.C(Cl)(=O)C(Cl)=O.[OH:11][CH2:12][CH2:13][N:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][C:21]=2[C:23]([O:25][CH3:26])=[O:24])[CH:16]=[N:15]1.C(N(CC)C(C)C)(C)C>C(Cl)Cl>[O:11]=[CH:12][CH2:13][N:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][C:21]=2[C:23]([O:25][CH3:26])=[O:24])[CH:16]=[N:15]1

참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 66899478methyl 1-(2-hydroxyethyl)-1H-indazole-7-carboxylate

생성물 1

HCID 86672700methyl 1-(2-oxoethyl)-1H-indazole-7-carboxylate수율 53%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

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온도
-78 °C

실험 절차

To a stirred solution of DMSO (0.4 mL, 5.2 mmol) and methylene chloride (2 mL) at −78° C. was added oxalyl chloride (0.3 mL, 3.1 mmol) dropwise. After 20 min, a solution of methyl 1-(2-hydroxyethyl)-1H-indazole-7-carboxylate (0.6 g, 2.6 mmol) from Step D above in methylene chloride (17 mL) was added and the mixture was stirred at −78° C. for 1.5 h. After N,N-diisopropylethylamine was added, the reaction was cooled to 0° C. and quenched with saturated aqueous ammonium chloride. The aqueous layer was extracted with methylene chloride and the organic extracts were dried (Na2SO4), filtered, concentrated under reduced pressure and purified by preparatory thin layer chromatography (30% ethyl acetate in hexanes) to give methyl 1-(2-oxoethyl)-1H-indazole-7-carboxylate (0.3 g, 53%): 1H NMR (500 MHz, CDCl3) δ 9.79 (s, 1H), 8.16 (s, 1H), 8.10-8.09 (m, 1H), 7.99-7.97 (m, 1H), 7.25-7.21 (m, 1H), 5.61 (s, 2H), 3.92 (s, 3H).

후처리

  1. temperaturethe reaction was cooled to 0° C.
  2. customquenched with saturated aqueous ammonium chloride
  3. extractionThe aqueous layer was extracted with methylene chloride
  4. dry with materialthe organic extracts were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. custompurified by preparatory thin layer chromatography (30% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-5236beb998884c6799cd03a85c41eee7
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09045501B2

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