Homoallyl bromide → HCID 178450298, compound

HRID 660153Notes

Reaction equation

HRID 660153 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][O:10][C:11]2[C:12]([C:16]3[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=3)=[N:13][NH:14][CH:15]=2)C=CC=CC=1.BrCCC=C.N1C=CC=C(C2C(O)=CN(COCC[Si](C)(C)C)N=2)C=1>C(OCC)C>[CH2:9]([O:10][C:11]1[C:12]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)=[N:13][NH:14][CH:15]=1)[CH2:8][CH:7]=[CH2:1]

Participants

5

Reactant 3

HCID 21241Homoallyl bromideHCID 57548087HCID 57548087, compoundHCID 178420268HCID 178420268, compound

Product 1

HCID 178450298HCID 178450298, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Compound 32D was prepared following the procedure as described for the synthesis of compound 32A (see Scheme 5) using 4-bromo-but-1-ene as the alkyl halogenide and 3-pyridin-3-yl-1-(2-trimethylsilanyl-1-ethoxymethyl)-1H-pyrazol-4-ol (30). Work-up and flash chromatography (diethyl ether) afforded compound 31 D. Yield 43% (oil, TLC diethyl ether Rf 0.37), which was subsequently deprotected (TBAF/THF) to afford 3-(4-but-3-enyloxy-1H-pyrazol-3-yl)-pyridine (32D).

Sources & evidence

ORD record
ord-f982a84d99ef4665b65ce44e56962f74
Source dataset
uspto-grants-2011_12
Patent number
US08084473B2

Reaction notes

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