Ammonium Acetate → HCID 58565368, compound

HRID 2175352Notes

Reaction equation

HRID 2175352 reaction equation
[C:1]([C:4]1[N:5]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=2)[C:6]2[C:11]([C:12]=1[C:13]#[N:14])=[CH:10][CH:9]=[CH:8][CH:7]=2)(=O)[CH3:2].C([O-])(=O)C.[NH4+].C([BH3-])#[N:28].[Na+]>CO.C(#N)C>[NH2:28][CH:1]([C:4]1[N:5]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=2)[C:6]2[C:11]([C:12]=1[C:13]#[N:14])=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH3:2]

Participants

6

Reactant 3

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 58565369HCID 58565369, compound

Product 1

HCID 58565368HCID 58565368, compoundYield 102.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 2-acetyl-1-(3-fluorophenyl)-1H-indole-3-carbonitrile (43 mg, 0.15 mmol) and ammonium acetate (0.119 g, 1.54 mmol) in methanol (1.5 mL) and acetonitrile (1.5 mL) was heated at 65° C. in a sealed tube for 1 hour. After cooling to room temperature, sodium cyanoborohydride (29 mg, 0.46 mmol) was added to the resultant mixture. The reaction was heated at 65° C. overnight. The reaction was then cooled to room temperature, quenched with saturated NaHCO3 solution, and extracted with dichloromethane. The combined organic layers were dried over MgSO4 and concentrated to give the desired product (43 mg), which was used directly in the next step. LCMS calculated for C17H15FN3(M+H)+: m/z=280.1. Found: 280.1.

Workup

  1. temperatureAfter cooling to room temperature
  2. temperatureThe reaction was heated at 65° C. overnight
  3. temperatureThe reaction was then 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-777ace9a5d914980aa6223faa6f4f734
Source dataset
uspto-grants-2015_06
Patent number
US09062055B2

Reaction notes

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