6-Iodopyridine-3-carboxylic acid → 6-(Prop-1-yn-1-yl)nicotinic acid

HRID 710472Notes

Reaction equation

HRID 710472 reaction equation
I[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1.I[C:12]1[CH:13]=C(C=C[C:20]=1CCC)C(O)=O>>[C:20]([C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1)#[C:12][CH3:13]

Participants

3

Reactant 2

HCID 8190626-Iodopyridine-3-carboxylic acidHCID 448288293-Iodo-4-propylbenzoic acid

Product 1

HCID 667263446-(Prop-1-yn-1-yl)nicotinic acidYield 45%

Procedure

When 6-iodonicotinic acid was substituted for the 3-iodo-4-propylbenzoic acid in Example 47, Step B, the similar process afforded the title compound in 45% yield, as yellow solid. 1H-NMR (CDCl3) 2.12 (s, 3H); 7.25 (broad s, 1H+H2O); 7.46 (dd, 1H, J=0.6, 7.6 Hz); 8.2 (dd, 1H, J=2.16, 6 Hz); 9.23 (dd, 1H, J=0.8, 1.4 Hz).

Sources & evidence

ORD record
ord-2abe0e9771bf47f3b6e4f093ccec56c1
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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