Tetrahydrofuran → HCID 86672701, compound

HRID 2168502Notes

Reaction equation

HRID 2168502 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([O:13][CH3:14])=[O:12])[CH:10]=1)[N:7]([CH2:15][CH:16](OC)[O:17]C)[N:6]=[CH:5]2.C1COCC1.C([O-])(O)=O.[Na+]>Cl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([O:13][CH3:14])=[O:12])[CH:10]=1)[N:7]([CH2:15][CH:16]=[O:17])[N:6]=[CH:5]2

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 516892Sodium BicarbonateHCID 66898762HCID 66898762, compound

Product 1

HCID 86672701HCID 86672701, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Methyl 5-chloro-1-(2,2-dimethoxyethyl)-1H-indazole-7-carboxylate (733 mg, 2.5 mmol) from Step B above was refluxed in 2 N HCl (8 mL) and THF (8 mL) until the reaction was complete by TLC (3-5 h). After cooling to room temperature, the pH of the reaction mixture was adjusted to 8 with NaHCO3, then extracted with ethyl acetate. The organic layers were combined, dried (Na2SO4), filtered, concentrated and purified by column chromatography (silica gel, 1:1 ethyl acetate/hexanes) to afford methyl 5-chloro-1-(2-oxoethyl)-1H-indazole-7-carboxylate as an off-white solid (472 mg, 76%): 1H NMR (300 MHz, CDCl3) δ 9.77 (s, 1H), 8.10 (s, 1H), 8.05 (s, 1H), 7.94 (s, 1H), 5.60 (s, 2H), 4.03 (d, J=8.4 Hz, 1H), 3.93 (s, 3H); MS (ESI+) m/z 253 (M+H).

Workup

  1. customwas complete by TLC (3-5 h)
  2. extractionextracted with ethyl acetate
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by column chromatography (silica gel, 1:1 ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-596b5c6cd8314776b98ca5250941a9a8
Source dataset
uspto-grants-2015_06
Patent number
US09045501B2

Reaction notes

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