Dimethylformamide → HCID 178509476, compound

HRID 913438Notes

Reaction equation

HRID 913438 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-177bd3faa4ff4870b556029cb7d24219
Source dataset
uspto-grants-2011_09
Patent number
US08026262B2

Reaction notes

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