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

HRID 2168556노트

반응식

HRID 2168556 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-50ffc04a1e5c49899b5986eb4f65eded
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09045501B2

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