Ammonium Acetate → HCID 58368572, compound

HRID 1192707Notes

Reaction equation

HRID 1192707 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([C:11](=O)[CH3:12])[C:8]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=2)=[C:7]2[C:3]=1[CH:4]=[N:5][NH:6]2.C([O-])(=O)C.[NH4+].C([BH3-])#[N:27].[Na+]>CO.C(#N)C>[Cl:1][C:2]1[CH:10]=[C:9]([CH:11]([NH2:27])[CH3:12])[C:8]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=2)=[C:7]2[C:3]=1[CH:4]=[N:5][NH:6]2

Participants

6

Reactant 3

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 58368514HCID 58368514, compound

Product 1

HCID 58368572HCID 58368572, compoundYield 99.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 1-[4-chloro-7-(3-fluorophenyl)-1H-indazol-6-yl]ethanone (2.365 g, 8.192 mmol), ammonium acetate (6.31 g, 81.9 mmol) and sodium cyanoborohydride (1.03 g, 16.4 mmol) in methanol (30 mL) and acetonitrile (30 mL) was heated at 65° C. overnight, in a sealed tube. The mixture was then cooled to room temperature and quenched with sat. sodium bicarbonate and then extracted with dichloromethane. The combined extracts were dried over magnesium sulfate and evaporated to dryness to give the crude product (2.37 g). LCMS calculated for C15H11ClFN2 (M−NH2)+: m/z=273.1; Found: 273.0.

Workup

  1. temperatureThe mixture was then cooled to room temperature
  2. customquenched with sat. sodium bicarbonate
  3. extractionextracted with dichloromethane
  4. dry with materialThe combined extracts were dried over magnesium sulfate
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-28a07c8ecc064c2fa69601ba55522a5a
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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