((1E)-prop-1-en-1-yl)boronic acid → 5-Methyl-6-propylnicotinic acid

HRID 1908778Notes

Reaction equation

HRID 1908778 reaction equation
[CH2:1]([C:5]1[C:13]([CH3:14])=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][N:6]=1)[CH:2](C)[CH3:3].C(OC(=O)C1C=C(C)C(Cl)=NC=1)C.C(/B(O)O)=C\C>>[CH3:14][C:13]1[C:5]([CH2:1][CH2:2][CH3:3])=[N:6][CH:7]=[C:8]([CH:12]=1)[C:9]([OH:11])=[O:10]

Participants

4

Reactant 3

HCID 6157276((1E)-prop-1-en-1-yl)boronic acidHCID 574371976-Chloro-5-methylnicotinic acid ethyl esterHCID 574372026-Isobutyl-5-methyl-nicotinic acid

Product 1

HCID 584180605-Methyl-6-propylnicotinic acid

Procedure

5-Methyl-6-propyl-nicotinic acid (1.85 g as hydrochloride) is prepared in analogy to 6-isobutyl-5-methyl-nicotinic acid from 6-chloro-5-methyl-nicotinic acid ethyl ester (2.0 g) and commercially available trans-1-propen-1-yl boronic acid (1.3 g); 1H NMR (D6-DMSO) δ 0.96 (t, J=7.3 Hz, 3H), 1.72 (m, 2H), 3.05 (t, J=7.5 Hz, 2H), 8.66 (m, 1H), 8.86 (d, J=1.5 Hz, 1H).

Sources & evidence

ORD record
ord-f83a1ce9d7504156a5cfd40f8bcdeed5
Source dataset
uspto-grants-2013_12
Patent number
US08598208B2

Reaction notes

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