Trimethylsilylacetylene → HCID 86295314, compound

HRID 2271489Notes

Reaction equation

HRID 2271489 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9]([O:24][CH3:25])=[N:10][CH:11]=[C:12]([CH2:14][N:15]3[CH:19]=[C:18]([Si](C)(C)C)[N:17]=[N:16]3)[CH:13]=2)[CH:5]=[CH:6][CH:7]=1.N(CC1C=C(C2C=CC=C(Cl)C=2)C(OC)=NC=1)=[N+]=[N-].C([Si](C)(C)C)#C.C(N(C(C)C)CC)(C)C>C1COCC1.O.[Cu]I>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9]([O:24][CH3:25])=[N:10][CH:11]=[C:12]([CH2:14][N:15]3[CH:19]=[CH:18][N:17]=[N:16]3)[CH:13]=2)[CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 66111TrimethylsilylacetyleneHCID 81531DiisopropylethylamineHCID 90415306HCID 90415306, compoundHCID 131732871HCID 131732871, compound

Product 1

HCID 86295314HCID 86295314, compoundYield 48%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

3-(3-Chlorophenyl)-2-methoxy-5-((4-(trimethylsilyl)-1H-1,2,3-triazol-1-yl)methyl)pyridine. To a solution of 5-(azidomethyl)-3-(3-chlorophenyl)-2-methoxypyridine (directly used from previous reaction) and ethynyltrimethylsilane (75.1 mg, 0.77 mmol) in THF (3 mL), water (1 mL), was added copper (I) iodide (19.4 mg, 0.10 mmol) and diisopropylethylamine (132 mg, 1.02 mmol). The mixture was stirred at room temperature for 2 h. The mixture was diluted with water and extracted in to DCM. The organic layers were combined, dried (Na2SO4), filtered and concentrated under reduced pressure. Purification (FCC, SiO2, 0-50% EtOAc/hexanes) afforded the title compound (92 mg, 48%). [M+H]=373.2.

Workup

  1. extractionextracted in to DCM
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customPurification (FCC, SiO2, 0-50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-816e1317864742b189e17058aef5b5f8
Source dataset
uspto-grants-2015_09
Patent number
US09120770B2

Reaction notes

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