Tetrahydrofuran → HCID 71295244, compound

HRID 868826Notes

Reaction equation

HRID 868826 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:9]=[CH:10][C:11]([O:16][CH2:17][CH:18]3[CH2:20][CH2:19]3)=[C:12]([CH:15]=2)[C:13]#[N:14])[CH:5]=[CH:4][N:3]=1.Cl.[NH:22]1[CH:26]=[C:25]([NH2:27])[CH:24]=[N:23]1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].C1COCC1>C(O)(C)(C)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O>[CH:18]1([CH2:17][O:16][C:11]2[CH:10]=[CH:9][C:8]([C:6]3[CH:5]=[CH:4][N:3]=[C:2]([NH:27][C:25]4[CH:26]=[N:22][NH:23][CH:24]=4)[CH:7]=3)=[CH:15][C:12]=2[C:13]#[N:14])[CH2:20][CH2:19]1

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 78034Pyrazole, 4-amino-, hydrochlorideHCID 2733832Lithium HexamethyldisilazideHCID 86729194HCID 86729194, compound

Product 1

HCID 71295244HCID 71295244, compoundYield 91.4%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

A solution of 5-(2-chloropyridin-4-yl)-2-cyclopropylmethoxybenzonitrile (0.25 g, 0.0878 mmol) in t-butanol (5 ml) is degassed with nitrogen for 5 min. 1H-Pyrazol-4-ylamine hydrochloride (0.12 g, 1.08 mmol), Josiphos (24.3 mg, 0.00439 mmol) and tris(dibenzylideneacetone)dipalladium(0) (40.0 mg, 0.00439 mmol) is then added. A solution of 1.6M lithium bis(trimethylsilyl)amide in THF (0.35 g, 2.1 mmol) is added dropwise. The mixture is irradiated in the microwave at 140° C. for 2 h. 30 ml of water are then added, and the mixture is filtered. The crude product is purified by chromatography, giving 26.6 mg of the desired product as brown solid;

Workup

  1. customThe mixture is irradiated in the microwave at 140° C. for 2 h
  2. filtrationthe mixture is filtered
  3. customThe crude product is purified by chromatography

Sources & evidence

ORD record
ord-d4edc4b65c034d38a8424f74c42f41c5
Source dataset
uspto-grants-2015_03
Patent number
US08969335B2

Reaction notes

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