Diisopropylethylamine → HCID 67261966, compound

HRID 2359046Notes

Reaction equation

HRID 2359046 reaction equation
Br[C:2]1[CH:7]=[C:6]([C:8]2[C:9]([C:17]3[S:18][C:19]([Cl:22])=[CH:20][CH:21]=3)=[N:10][N:11]([CH:13]([CH2:15][CH3:16])[CH3:14])[CH:12]=2)[CH:5]=[CH:4][N:3]=1.[CH:23]1([C:26]#[CH:27])[CH2:25][CH2:24]1.C(N(CC)C(C)C)(C)C>O1CCCC1.[Cu](I)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>[CH:13]([N:11]1[CH:12]=[C:8]([C:6]2[CH:5]=[CH:4][N:3]=[C:2]([C:27]#[C:26][CH:23]3[CH2:25][CH2:24]3)[CH:7]=2)[C:9]([C:17]2[S:18][C:19]([Cl:22])=[CH:20][CH:21]=2)=[N:10]1)([CH2:15][CH3:16])[CH3:14]

Participants

7

Reactant 3

HCID 81531DiisopropylethylamineHCID 138823CyclopropylacetyleneHCID 86657922HCID 86657922, compound

Product 1

HCID 67261966HCID 67261966, compoundYield 51%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 2-bromo-4-[1-sec-butyl-3-(5-chloro-2-thienyl)-1H-pyrazol-4-yl]pyridine (0.18 mmol) in 2 mL of tetrahydrofurane was added cyclopropylacetylene (0.71 mmol), copper iodide (0.053 mmol), dichlorobis(triphenylphosphine)palladium (II) (0.053 mmol) and N,N-diisopropylethlamine (0.88 mmol). The resulting mixture was stirred in the microwave at 120° C. for 3 min. The solvent was then evaporated and the residue was purified by chromatography on silica gel (hepthane:ethyl acetate 5:1 to 2:1) to afford 35 mg of 4-[1-sec-butyl-3-(5-chloro-2-thienyl)-1H-pyrazol-4-yl]-2-(cyclopropylethynyl)pyridine (51% yield).

Workup

  1. customThe solvent was then evaporated
  2. customthe residue was purified by chromatography on silica gel (hepthane:ethyl acetate 5:1 to 2:1)

Sources & evidence

ORD record
ord-e52cbb50775d4826a0298c6a7988d978
Source dataset
uspto-grants-2014_04
Patent number
US08685974B2

Reaction notes

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