3-Ethyl-1-pentyn-3-ol → 7-{[4-(1-ethyl-1-hydroxypropyl)-1H-1,2,3-triazol-1-yl]methyl}-4-phenylquinoline-2-carbonitrile

HRID 2422531Notes

Reaction equation

HRID 2422531 reaction equation
[N:1]([CH2:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:10][C:11]([C:15]#[N:16])=[N:12]2)=[CH:7][CH:6]=1)=[N+:2]=[N-:3].[CH2:23]([C:25]([OH:30])([CH2:28][CH3:29])[C:26]#[CH:27])[CH3:24].C(N(C(C)C)CC)(C)C>C1COCC1.[Cu](I)I>[CH2:26]([C:25]([C:23]1[N:3]=[N:2][N:1]([CH2:4][C:5]2[CH:14]=[C:13]3[C:8]([C:9]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)=[CH:10][C:11]([C:15]#[N:16])=[N:12]3)=[CH:7][CH:6]=2)[CH:24]=1)([OH:30])[CH2:28][CH3:29])[CH3:27]

Participants

6

Reactant 3

HCID 226983-Ethyl-1-pentyn-3-olHCID 81531DiisopropylethylamineHCID 59774860HCID 59774860, compound

Product 1

HCID 250576617-{[4-(1-ethyl-1-hydroxypropyl)-1H-1,2,3-triazol-1-yl]methyl}-4-phenylquinoline-2-carbonitrile

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 7-(azidomethyl)-4-phenylquinoline-2-carbonitrile (100 mg, 0.35 mmol), 3-ethylpent-1-yn-3-ol (47 mg, 0.42 mmol), copper iodide (100 mg, 0.52 mmol) and diisopropylethylamine (305 μL, 1.75 mmol) in THF (4 mL) was stirred at rt for 6 h. The reaction was quenched with saturated aqueous NH4Cl and extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. Purification on silica gel (eluting with acetone/dichloromethane, 2:8) gave the title compound. MS (+ESI): 398 (M+H)+.

Workup

  1. customThe reaction was quenched with saturated aqueous NH4Cl
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification on silica gel (eluting with acetone/dichloromethane, 2:8)

Sources & evidence

ORD record
ord-e99e92ebb877478381c7730ad7e782a5
Source dataset
uspto-grants-2011_06
Patent number
US07960409B2

Reaction notes

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