Borane → HCID 68753043, compound

HRID 1615260Notes

Reaction equation

HRID 1615260 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([C:11](O)=[O:12])[CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][NH:6]2.B>C1COCC1>[Cl:1][C:2]1[CH:10]=[C:9]([CH2:11][OH:12])[CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][NH:6]2

Participants

4

Reactant 2

HCID 6331BoraneHCID 247283964-Chloro-1H-indazole-6-carboxylic acid

Product 1

HCID 68753043HCID 68753043, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-chloro-1H-indazole-6-carboxylic acid (100 mg, 0.5 mmol) in THF (1 mL) was cooled to 0° C. under argon. Borane (1.4 mL, 1.4 mmol) was added dropwise and the solution was stirred overnight at rt. The reaction was quenched with ice cold sat. sodium bicarbonate, extracted with ethyl acetate (3×10 mL), dried over MgSO4 and concentrated to give the title compound as a white solid (60 mg, 66%). MS ESI [M+H]+, calcd for [C8H7ClN2O+H]+ 183.0; found m/z 183.0.

Workup

  1. customThe reaction was quenched with ice cold sat. sodium bicarbonate
  2. extractionextracted with ethyl acetate (3×10 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c7796a0c2ea847ae85866db28b91665c
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

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