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

HRID 2168494Notes

Reaction equation

HRID 2168494 reaction equation
F[C:2]1[C:10]([CH:11]=O)=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([O-:6])=[O:5].[NH:13]([CH2:15][CH2:16][OH:17])[NH2:14].[CH3:18]O>C(OCC)(=O)C>[OH:17][CH2:16][CH2:15][N:13]1[C:2]2[C:10](=[CH:9][CH:8]=[CH:7][C:3]=2[C:4]([O:6][CH3:18])=[O:5])[CH:11]=[N:14]1

Participants

5

Reactant 3

HCID 887MethanolHCID 80172-HydrazinoethanolHCID 866726992-Fluoro-3-formylbenzoate

Product 1

HCID 66899478methyl 1-(2-hydroxyethyl)-1H-indazole-7-carboxylateYield 95%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 2-fluoro-3-formylbenzoate (0.5 g, 2.8 mmol) in methanol (4 mL) was added 2-hydrazinoethanol (0.2 mL, 2.8 mmol) and the mixture was stirred at room temperature. After the starting material was consumed, the solution was transferred to a microwave tube and microwaved at 150° C. for 5 h. The crude reaction was diluted with ethyl acetate, washed with water, dried (Na2SO4), filtered, concentrated under reduced pressure and purified by column chromatography (silica gel, 0% to 50% ethyl acetate in hexanes) to afford methyl 1-(2-hydroxyethyl)-1H-indazole-7-carboxylate (0.6 g, 95%): 1H NMR (500 MHz, CDCl3) δ 8.04-8.02 (m, 1H), 8.00-7.98 (m, 1H), 7.95-7.93 (m, 1H), 4.87-4.80 (m, 2H), 4.14-4.10 (m, 2H), 3.99 (s, 3H); MS (ESI+) m/z 221 (M+H).

Workup

  1. customAfter the starting material was consumed
  2. customthe solution was transferred to a microwave tube
  3. custommicrowaved at 150° C. for 5 h
  4. customThe crude reaction
  5. washwashed with water
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. custompurified by column chromatography (silica gel, 0% to 50% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-1b89432477694396a95c5f2780aa809c
Source dataset
uspto-grants-2015_06
Patent number
US09045501B2

Reaction notes

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