2-Hydrazinoethanol → methyl 1-(2-hydroxyethyl)-1H-indazole-7-carboxylate

HRID 2369934노트

반응식

HRID 2369934 반응식
F[C:2]1[C:11]([CH:12]=O)=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[OH:14][CH2:15][CH2:16][NH:17][NH2:18]>CO>[OH:14][CH2:15][CH2:16][N:17]1[C:2]2[C:11](=[CH:10][CH:9]=[CH:8][C:3]=2[C:4]([O:6][CH3:7])=[O:5])[CH:12]=[N:18]1

참가 물질

4

반응물 2

HCID 80172-HydrazinoethanolHCID 57423810Methyl 2-fluoro-3-formylbenzoate

생성물 1

HCID 66899478methyl 1-(2-hydroxyethyl)-1H-indazole-7-carboxylate수율 65%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A mixture of methyl 2-fluoro-3-formylbenzoate (3.6 g, 19.9 mmol) from Step C above and hydroxy ethyl hydrazine (1.5 g, 19.9 mmol) in MeOH (16 mL) was irradiated with microwaves at 150° C. for 1.5 h. The reaction mixture was cooled and partitioned between H2O and ethyl acetate. The aqueous phase was extracted with additional ethyl acetate and then the combined organic extracts were dried (Na2SO4) filtered, concentrated and purified by column chromatography (silica gel, 70:30 hexanes/ethyl acetate) to afford methyl 1-(2-hydroxyethyl)-1H-indazole-7-carboxylate as a yellow solid (2.83 g, 65%): 1H NMR (500 MHz, CDCl3) δ 8.13 (s, 1H), 7.99 (d, J=7.5 Hz, 1H), 7.94 (d, J=8.0 Hz, 1H); 7.18 (t, J=8.5 Hz, 1H), 4.84 (t, J=5.0 Hz, 2H), 4.13-4.07 (m, 2H), 3.99 (s, 3H), 3.20-3.10 (m, 1H).

후처리

  1. customwas irradiated with microwaves at 150° C. for 1.5 h
  2. temperatureThe reaction mixture was cooled
  3. custompartitioned between H2O and ethyl acetate
  4. extractionThe aqueous phase was extracted with additional ethyl acetate
  5. dry with materialthe combined organic extracts were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by column chromatography (silica gel, 70:30 hexanes/ethyl acetate)

출처 및 근거

ORD 기록
ord-640bd481acb6430b847e65da0319016e
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08710046B2

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