Diisopropylethylamine → HCID 22592273, compound

HRID 22871Notes

Reaction equation

HRID 22871 reaction equation
[CH:1]#[C:2][CH2:3][N:4]1[CH:8]=[CH:7][N:6]=[N:5]1.[C:9]([C:11]1[CH:27]=[CH:26][C:14]([CH2:15][NH:16][C:17](=[O:25])[C:18]2[CH:23]=[CH:22][CH:21]=[C:20](I)[CH:19]=2)=[CH:13][CH:12]=1)#[N:10].C(N(C(C)C)CC)(C)C>CN(C)C=O.C1COCC1.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:9]([C:11]1[CH:12]=[CH:13][C:14]([CH2:15][NH:16][C:17](=[O:25])[C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:1]#[C:2][CH2:3][N:4]3[CH:8]=[CH:7][N:6]=[N:5]3)[CH:19]=2)=[CH:26][CH:27]=1)#[N:10]

Participants

8

Reactant 3

HCID 81531DiisopropylethylamineHCID 127095801-(prop-2-yn-1-yl)-1H-1,2,3-triazoleHCID 22592288HCID 22592288, compound

Product 1

HCID 22592273HCID 22592273, compoundYield 36.4%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
55 °C

Procedure

A solution of 1-propyn-3-yl-1H-[1,2,3]triazol (0.086 g, 0.8 mmol) in N,N-dimethylformamide (“DMF”, 1 mL) was treated with the N-(4-cyano-benzyl)-3-iodo-benzamide (0.225 g, 0.62 mmol) prepared in Step (1), diisopropylethylamine (0.32 g, 2.5 mmol), copper (I) iodide (0.024 g, 0.013 mmol), and dichlorobis(triphenylphosphine)palladium (II) (0.025 g, 0.004 mmol), respectively. The reaction mixture was stirred under nitrogen atmosphere for 5 hours at 55° C., then cooled to room temperature. The crude reaction mixture was diluted with THF (5 mL) and passed through a pad of silica gel (elution with THF). The partially purified product obtained was further purified using silica gel chromatography (elution with THF/hexane [3:1]) to give the title compound (0.077 g, 36%) as cream color solid. 1H-NMR (CDCl3/DMSO-d6) δ 8.3 (m, 1H), 7.9 (s, 1H), 7.8 (m, 2H), 7.6 (s, 1H), 7.4 (m, 3H), 7.3 (m, 2H), 5.3 (s, 2H), 4.5 (d, 2H) ppm. Mp 145° C.-147° C.

Workup

  1. temperaturecooled to room temperature
  2. customThe crude reaction mixture
  3. customThe partially purified product obtained
  4. customwas further purified
  5. washsilica gel chromatography (elution with THF/hexane [3:1])

Sources & evidence

ORD record
ord-6ec05802ceb740d583629ea36e7e75b4
Source dataset
uspto-grants-2005_02
Patent number
US06849648B2

Reaction notes

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