HCID 66597924, compound → HCID 66598268, compound

HRID 334699Notes

Reaction equation

C([N:5]1[C:9](C)=[C:8]([C:11]2[CH:16]=[CH:15]C=CC=2)C=N1)CC#C.[CH2:17]([N:21]1[CH:25]=[C:24]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:23]([CH3:32])=[N:22]1)[CH2:18][C:19]#[CH:20].CC1N(CCC#CC2C=CC=CN=2)N=CC=1C1C=CC=CC=1>>[CH3:32][C:23]1[C:24]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:25][N:21]([CH2:17][CH2:18][C:19]#[C:20][C:9]2[CH:8]=[CH:11][CH:16]=[CH:15][N:5]=2)[N:22]=1

Participants

Reactant 3

HCID 66597924HCID 66597924, compound

HCID 86086787HCID 86086787, compound

HCID 86086789HCID 86086789, compound

Product 1

HCID 66598268HCID 66598268, compoundYield 10%

Procedure

The title compounds were prepared in accordance with the general method of Example 1, from 255 mg (1.21 mmol) of 1-but-3-ynyl-5-methyl-4-phenyl-1H-pyrazole and 1-but-3-ynyl-3-methyl-4-phenyl-1H-pyrazole. The crude residue was purified by flash chromatography (DCM/MeOH 99:1 to 98:2) to yield 33 mg (0.11 mol, 10%) of 2-(4-(3-methyl-4-phenyl-1H-pyrazol-1-yl)but-1-ynyl)pyridine and 2-(4-(5-methyl-4-phenyl-1H-pyrazol-1-yl)but-1-ynyl)pyridine as a orange oil.

Workup

customThe crude residue was purified by flash chromatography (DCM/MeOH 99:1 to 98:2)

Sources & evidence

ORD record: ord-201e63342694491f9f2773765da84198
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08883826B2

Reaction notes

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