2-Acetylpyridine → 2-(Pyridin-2-yl)but-3-yn-2-ol

HRID 1398529Notes

Reaction equation

HRID 1398529 reaction equation
[C:1]([C:3]1([OH:12])[C:7]2=[N:8][CH:9]=[CH:10][CH:11]=[C:6]2C[CH2:4]1)#[CH:2].C(C1C=CC=CN=1)(=O)C>>[N:8]1[CH:9]=[CH:10][CH:11]=[CH:6][C:7]=1[C:3]([OH:12])([C:1]#[CH:2])[CH3:4]

Participants

3

Reactant 2

HCID 142862-AcetylpyridineHCID 866695787-ethynyl-6,7-dihydro-5H-cyclopenta[b]pyridin-7-ol

Product 1

HCID 167625022-(Pyridin-2-yl)but-3-yn-2-ol

Procedure

The title compound was prepared using the method described for the preparation of 7-ethynyl-5H,6H-cyclopenta[b]pyridin-7-ol, by replacing 5,6-dihydro-7H-cyclopenta[b]pyridin-7-one with 2-acetylpyridine; 1H NMR (500 MHz, CDCl3) delta 1.80 (3H, s), 2.55 (1H, s), 5.50 (1H, s), 7.20-7.32 (1H, m), 7.62 (1H, d, J=7.88 Hz), 7.78 (1 H, td, J=7.72, 1.58 Hz), 8.54 (1H, d, J=4.73 Hz); LC-MS: m/z=+147.9 (M+H)+.

Sources & evidence

ORD record
ord-01bee8723f00436da66bfeaff43103da
Source dataset
uspto-grants-2014_12
Patent number
US08901313B2

Reaction notes

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