Ammonium Acetate → HCID 58565358, compound

HRID 2175323Notes

Reaction equation

HRID 2175323 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:18](=O)[CH3:19])[N:6]2[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=1.C([O-])(=O)C.[NH4+].C([BH3-])#[N:27].[Na+]>CO.C(#N)C>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH:18]([NH2:27])[CH3:19])[N:6]2[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=1

Participants

6

Reactant 3

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 58565352HCID 58565352, compound

Product 1

HCID 58565358HCID 58565358, compoundYield 84.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 1-[4-chloro-1-(3-fluorophenyl)-1H-indol-2-yl]ethanone (0.13 g, 0.45 mmol) and ammonium acetate (0.348 g, 4.52 mmol) in methanol (2.0 mL) and acetonitrile (2.0 mL) was heated at 65° C. in a sealed tube for 30 minutes. After cooling to room temperature, to the resultant mixture was added sodium cyanoborohydride (57 mg, 0.91 mmol). The reaction was heated at 65° C. for another 4 hours. After cooling to room temperature, the reaction was quenched with aqueous saturated NaHCO3 solution and then extracted with dichloromethane. The combined organic layers were dried over MgSO4 and concentrated to give the desired product (0.11 g), which was used directly in the next step. LCMS calculated for C16H12ClFN(M-NH2)+: m/z=272.1. Found: 272.0.

Workup

  1. temperatureThe reaction was heated at 65° C. for another 4 hours
  2. temperatureAfter cooling to room temperature
  3. customthe reaction was quenched with aqueous saturated NaHCO3 solution
  4. extractionextracted with dichloromethane
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5964844982254854926554c2220f49f9
Source dataset
uspto-grants-2015_06
Patent number
US09062055B2

Reaction notes

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