Methanol → HCID 59596293, compound

HRID 2264776Notes

Reaction equation

HRID 2264776 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:15]=[C:16]([Cl:18])[N:17]=1)[C:5]([C:7]1[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=1[C:9]#[N:10])=O.CC(C)C[S:22]([NH2:24])=[O:23].[CH3:26]O.C(=O)([O-])O.[Na+].O1[CH2:37][CH2:36][CH2:35]C1>[O-]CC.[Ti+4].[O-]CC.[O-]CC.[O-]CC>[C:9]([C:8]1[CH:11]=[CH:12][CH:13]=[CH:14][C:7]=1/[C:5](/[C:4]1[CH:3]=[C:2]([Cl:1])[N:17]=[C:16]([Cl:18])[CH:15]=1)=[N:24]/[S:22]([C:36]([CH3:35])([CH3:37])[CH3:26])=[O:23])#[N:10]

Participants

7

Reactant 5

HCID 887MethanolHCID 8028TetrahydrofuranHCID 516892Sodium BicarbonateHCID 219598541621232-55-02×HCID 59596256HCID 59596256, compound

Product 1

HCID 59596293HCID 59596293, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 76524Titanium tetraethoxideCatalyst2×

Procedure

Titanium (IV) ethoxide (1M in tetrahydrofuran, 10.2 mL, 10.2 mmol) was added to a solution of 2-(2,6-dichloroisonicotinoyl)benzonitrile (Scheme #19, A, 1.0 g, 3.3 mmol) in tetrahydrofuran (5 mL) at room temperature. After 5 minutes 2-methyl-propanesulfinamide (0.48 g, 3.96 mmol) was added and the reaction mixture was refluxed over night. Additional amounts of titanium (IV) ethoxide (1M in tetrahydrofuran, 3.0 mL, 3.0 mmol) and 2-methyl-propanesulfinamide (0.2 g, 1.6 mmol) were added and the reaction mixture was refluxed for 5 h. After cooled to room temperature methanol (5 mL) and saturated aqueous sodium hydrogen carbonate (0.1 mL) added to the reaction mixture. A precipitation occurred and the crude was filtered through a pad of sodium sulfate before evaporation. Purification by flash chromatography using a stepwise gradient of ethylacetate in heptane afforded the title compound in 44% yield. 1H NMR (CDCl3) δ 7.85-7.78 (m, 1 H), 7.78-7.70 (m, 1 H), 7.68-7.61 (m, 1 H), 7.44-7.35 (m, 1 H), 7.32 (s, 2 H), 1.38 (s, 9 H). MS (API) m/z 380 [M+1]+.

Workup

  1. customat room temperature
  2. temperaturethe reaction mixture was refluxed over night
  3. temperaturethe reaction mixture was refluxed for 5 h
  4. additionadded to the reaction mixture
  5. customA precipitation
  6. filtrationthe crude was filtered through a pad of sodium sulfate before evaporation
  7. customPurification by flash chromatography

Sources & evidence

ORD record
ord-382521745b8645d4abbcad083c5d0892
Source dataset
uspto-grants-2010_12
Patent number
US07855213B2

Reaction notes

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