3-Pyridineacetic acid → HCID 12999592, compound

HRID 660141Notes

Reaction equation

HRID 660141 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][C:8]([OH:10])=O)[CH:2]=1.C[N-]OC.[Li][CH2:16][CH2:17][CH2:18][CH3:19]>>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][C:8](=[O:10])[CH2:16][CH2:17][CH2:18][CH3:19])[CH:2]=1

Participants

4

Reactant 3

HCID 1083-Pyridineacetic acidHCID 53630747Methoxy-methyl amideHCID 178418339Butyllithium

Product 1

HCID 12999592HCID 12999592, compound

Procedure

In another example of the general procedure (scheme 2), readily available pyridin-3-yl-acetic acid (10) is converted to the N-methyl-N-methoxyamide derivate (12), which is reacted with BuLi to produce 1-pyridin-3-yl-hexan-2-one (13). N,N-dimethylformamide dimethylacetal treatment of 13 furnished the enamine (14) which is converted to the pyrazol (15). The synthesis of 3-(4-Butyl-1H-pyrazol-3-yl)-1,2,5,6-tetrahydro-1-methylpyridine (16) is illustrated in scheme 2 according to the two step sequence shown in scheme 1.

Sources & evidence

ORD record
ord-c7300da0306f4503aa3ababc126f085b
Source dataset
uspto-grants-2011_12
Patent number
US08084473B2

Reaction notes

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