Sodium Hydroxide → HCID 57524281, compound

HRID 623814Notes

Reaction equation

HRID 623814 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]2[N:17]=[CH:16][NH:15][N:14]=2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[C:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=1)#[CH:19].[OH-].[Na+].C(OCC)(=O)C.CCCCCC>CN(C=O)C.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]2[N:17]=[CH:16][N:15](/[CH:19]=[CH:18]\[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=3)[N:14]=2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 137268EthynylpyridineHCID 21226206Ethyl acetate hexaneHCID 178488015HCID 178488015, compound

Product 1

HCID 57524281HCID 57524281, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
77.5 °C

Procedure

In a 25 mL, 3 Neck round-bottomed flask equipped with nitrogen inlet and a rubber septum, 3-(3-methoxy-5-(trifluoromethyl)phenyl)-1H-1,2,4-triazole (0.25 g, 1.0 eq.), 2-ethynylpyridine (0.1 ml, 1.0 eq.) and sodium hydroxide (0.1028 g, 2.5 eq.) were dissolved in DMF (5.0 mL). The reaction mixture was stirred at 75-80° C. The progress of the reaction was followed by TLC analysis on silica gel with 50% ethyl acetate-hexane as mobile phase which shows that starting material was consumed after 15 h. Reaction mixture was diluted by water and extracted with ethyl acetate, combined organic layer was dried over sodium sulphate and distilled under reduce pressure (25° C., 20 mmHg) to obtain crude material. The crude compound was purified by column chromatography using 60/120 silica gel and ethyl acetate in hexane as mobile phase. The column was packed in Hexane and started eluting in ethyl acetate in gradient manner starting with fraction collection. The compound started eluting from 18% ethyl acetate in hexane. Fractions containing such TLC profile were collected together to obtain pure compound 0.005 g; LCMS (%): Retention time 3.476 min (97.44%); (Z)-2-(2-(3-(3-methoxy-5-(trifluoromethyl)phenyl)-1H-1H-1,2,4-triazole-1-yl)vinyl)pyridine: 1H NMR (400 MHz, DMSO) δ: 9.61 (s, 1H), 8.67-8.68 (d, 1H, J=4.8 Hz), 8.03 (S 1H), 7.86 (s, 1H), 7.71-7.76 (doublet of triplet, 1H), 7.30-7.732 (d, 1H, J=8 Hz), 7.20 (s, 1H), 7.14-7.16 (d, 1H, J=10.4 Hz), 6.40-6.42 (d, 1H, J=10.8 Hz), 3.94 (s, 1H). LCMS for C17H13F3N4O [M+H]+ 1345.3 found at 346.8 at 3.476 min (LCMS: 97.44%).

Workup

  1. customIn a 25 mL, 3 Neck round-bottomed flask equipped with nitrogen inlet
  2. customwas consumed after 15 h
  3. customReaction mixture
  4. extractionextracted with ethyl acetate
  5. dry with materialwas dried over sodium sulphate
  6. distillationdistilled
  7. custompressure (25° C., 20 mmHg)
  8. customto obtain crude material
  9. customThe crude compound was purified by column chromatography
  10. washstarted eluting in ethyl acetate in gradient manner
  11. customstarting with fraction collection
  12. washThe compound started eluting from 18% ethyl acetate in hexane
  13. additionFractions containing such TLC profile
  14. customwere collected together

Sources & evidence

ORD record
ord-72e83af5e02a4291af826b381ee46c02
Source dataset
uspto-grants-2016_04
Patent number
US09303000B2

Reaction notes

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