1,2-Dichloroethane → methyl 1H-indazole-6-carboxylate

HRID 14163

Reaction equation

HRID 14163 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:10]([OH:12])=[O:11])[CH:8]=2)[CH:3]=[N:2]1.[CH2:13](Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C>C(Cl)Cl.CO>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:10]([O:12][CH3:13])=[O:11])[CH:8]=2)[CH:3]=[N:2]1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 162279381H-indazole-6-carboxylic acid

Product 1

HCID 286535methyl 1H-indazole-6-carboxylateYield 87.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

To a mixture of 1H-indazole-6-carboxylic acid (1.0 g) in methylene chloride (15 mL) was added EDC (1.8 g), HOBT (1.27 g), and triethylamine (1.29 mL). The mixture was heated to 40° C. for 30 minutes at which time methanol (10.0 mL) was added. The mixture was stirred at 40° C. for 18 h. The mixture was removed from heat, cooled to room temperature and poured into methylene chloride. The mixture was washed twice with water then brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 0.955 g of the title compound: 1H NMR (CDCl3) δ 3.98, 7.81, 7.86, 8.16, 8.29, 10.6.

Workup

  1. additionwas added
  2. customThe mixture was removed
  3. temperaturefrom heat
  4. temperaturecooled to room temperature
  5. additionpoured into methylene chloride
  6. washThe mixture was washed twice with water
  7. dry with materialbrine, dried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6a1bc93ee637409f95728a186a28d160
Source dataset
uspto-grants-2010_06
Patent number
US07727997B2

Linked notes

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