Ethyl orthoformate → HCID 49862793, compound

HRID 2246446Notes

Reaction equation

HRID 2246446 reaction equation
[NH2:1][C:2]1[C:3]([C:19]#[N:20])=[N:4][C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=2)=[CH:6][C:7]=1[NH2:8].[CH:21](OCC)(OCC)OCC>C(#N)C.[O-]S(C(F)(F)F)(=O)=O.[Yb+3].[O-]S(C(F)(F)F)(=O)=O.[O-]S(C(F)(F)F)(=O)=O>[F:17][C:15]([F:18])([F:16])[C:11]1[CH:10]=[C:9]([C:5]2[N:4]=[C:3]([C:19]#[N:20])[C:2]3[N:1]=[CH:21][NH:8][C:7]=3[CH:6]=2)[CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 31214Ethyl orthoformateHCID 58938115HCID 58938115, compound

Product 1

HCID 49862793HCID 49862793, compoundYield 93.6%

Reagents, catalysts & solvents 2

HCID 2733225Ytterbium triflateCatalystHCID 6342AcetonitrileSolvent

Procedure

3,4-Diamino-6-(3-trifluoromethyl-phenyl)-pyridine-2-carbonitrile (120 mg, 0.43 mmol) was suspended in acetonitrile (5 ml) and the vessel was purged with nitrogen. Ytterbium triflate (5 mg, 0.009 mmol) and triethyl orthoformate (214 μl, 1.29 mmol) were added and the resulting orange suspension was heated at reflux for 1 hour. Reaction mixture was concentrated in vacuo to give the title compound as a yellow solid (116 mg). 1H NMR (MeOD): δ 8.55 (s, 1H), 8.35-8.41 (m, 3H), 7.71-7.76 (m, 2H). MS m/z 288.9 (M+1).

Workup

  1. customthe vessel was purged with nitrogen
  2. temperaturethe resulting orange suspension was heated
  3. temperatureat reflux for 1 hour
  4. customReaction mixture
  5. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-6bfbb9d086194f4db8e2b3c5b1f9a669
Source dataset
uspto-grants-2010_03
Patent number
US07687515B2

Reaction notes

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