Ammonium Acetate → HCID 58565367, compound

HRID 2175334Notes

Reaction equation

HRID 2175334 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=[C:9]2[C:17](=O)[CH3:18])[CH:5]=[CH:6][CH:7]=1.C([O-])(=O)C.[NH4+].C([BH3-])#[N:26].[Na+]>CO.C(#N)C>[F:1][C:2]1[CH:3]=[C:4]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=[C:9]2[CH:17]([NH2:26])[CH3:18])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 58565344HCID 58565344, compound

Product 1

HCID 58565367HCID 58565367, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 1-[1-(3-fluorophenyl)-1H-indol-2-yl]ethanone (0.40 g, 1.6 mmol) and ammonium acetate (1.22 g, 15.8 mmol) in methanol (5.0 mL) and acetonitrile (5.0 mL) was heated at 65° C. in a sealed tube for 30 minutes. After cooling to room temperature, sodium cyanoborohydride (0.20 g, 3.2 mmol) was added to the resultant mixture. The reaction was heated at 65° C. overnight. The reaction was cooled to room temperature and quenched with saturated NaHCO3 solution and extracted with dichloromethane. The combined organic layers were dried over MgSO4 and concentrated to give crude product (0.39 g, 97%), which was used directly in the next step. LCMS calculated for C16H13FN (M-NH2)+: m/z=238.1. Found: 238.1.

Workup

  1. temperatureAfter cooling to room temperature
  2. temperatureThe reaction was heated at 65° C. overnight
  3. temperatureThe reaction was cooled to room temperature
  4. customquenched with saturated NaHCO3 solution
  5. extractionextracted with dichloromethane
  6. dry with materialThe combined organic layers were dried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c13360af32504428b397bc754e9f84dd
Source dataset
uspto-grants-2015_06
Patent number
US09062055B2

Reaction notes

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