Dimethylformamide → HCID 178509476, compound

HRID 1188365Notes

Reaction equation

HRID 1188365 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[C:11]([C:12]#[N:13])=[CH:10][CH:9]=[C:8]2[C:4]=1[CH:5]=[CH:6][NH:7]2.[CH3:16][C:17]([O-])=O.[Na+].[NH2:21][OH:22].Cl.C([O-])(O)=O.[Na+].C[N:30](C=O)C>O>[C:12]([C:11]1[C:3]([C:2]([F:14])([F:1])[F:15])=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:16][C:17](=[NH:30])[NH:21][OH:22])[CH:6]=[CH:5]2)#[N:13]

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 517045Sodium AcetateHCID 674054494-(trifluoromethyl)-1H-indole-5-carbonitrile

Product 1

HCID 178509476HCID 178509476, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 4-(trifluoromethyl)-1H-indole-5-carbonitrile (0.210 g, 0.85 mmol) in DMF (15 mL), was added NaOAc/3H2O (0.346 g, 2.54 mmol) and H2NOH/HCl (0.176 g, 2.54 mmol). The resulting mixture was stirred at rt for 15 h. H2O (30 mL) and sat'd aqueous NaHCO3 (45 mL) were added to the reaction mixture. Extraction with Et2O (3×50 mL) was followed by washing with brine, drying (Na2SO4), filtration, and concentration in vacuo. Trituration with hexanes/CH2Cl2 afforded 0.282 g of the title compound in good purity: 1NMR (400 MHz, CDCl3) δ 7.71 (d, J=8.6 Hz, 1H), 7.51 (d, J=8.6 Hz, 1H), 7.42 (d, J=3.4 Hz, 1H), 6.75 (m, 1H), 4.80 (s, 2H); MS (ESI): m/z 283 (M+1).

Workup

  1. additionwere added to the reaction mixture
  2. extractionExtraction with Et2O (3×50 mL)
  3. washby washing with brine
  4. customdrying
  5. filtration(Na2SO4), filtration, and concentration in vacuo

Sources & evidence

ORD record
ord-c6a97c91a2974ed091b4e64298e79f9e
Source dataset
uspto-grants-2014_03
Patent number
US08673948B2

Reaction notes

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