2,5-Dibromo-4-methylpyridine → 5-Ethyl-4-methyl-pyridine-2-carboxylic acid ethyl ester

HRID 1908839Notes

Reaction equation

HRID 1908839 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[C:10]([CH3:12])[C:9]([CH2:13][CH:14](C)C)=[CH:8][N:7]=1)=[O:5])[CH3:2].BrC1C=C(C)C(Br)=CN=1>>[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[C:10]([CH3:12])[C:9]([CH2:13][CH3:14])=[CH:8][N:7]=1)=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 27344292,5-Dibromo-4-methylpyridineHCID 670270295-Isobutyl-4-methyl-pyridine-2-carboxylic acid ethyl ester

Product 1

HCID 670271415-Ethyl-4-methyl-pyridine-2-carboxylic acid ethyl ester

Procedure

5-Ethyl-4-methyl-pyridine-2-carboxylic acid ethyl ester is prepared in analogy to 5-isobutyl-4-methyl-pyridine-2-carboxylic acid ethyl ester starting from 2,5-dibromo-4-picoline; LC-MS: tR=0.70 min, [M+1]+=193.99; 1H NMR (CDCl3): δ 1.25 (t, J=7.8 Hz, 3H), 1.45 (t, J=7.0 Hz, 3H), 2.39 (s, 3H), 2.72 (q, J=7.5 Hz, 2H), 4.48 (q, J=7.0 Hz, 2H), 7.92 (s, 1H), 8.49 (s, 1H).

Sources & evidence

ORD record
ord-67219aa058c045f398a14fde33328a79
Source dataset
uspto-grants-2013_12
Patent number
US08598208B2

Reaction notes

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