3-(Benzyloxy)pyridin-2-ol → 1-(4-Azidobutyl)-3-benzyloxypyridine-2-one

HRID 539536Notes

Reaction equation

HRID 539536 reaction equation
[CH2:1]([O:8][C:9]1[C:10](=[O:15])[NH:11][CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CS(OC[CH:22]([N:25]=[N+:26]=[N-:27])[CH2:23][CH3:24])(=O)=O.N([CH2:31]CN1C=CC=C(OC)C1=O)=[N+]=[N-]>>[N:25]([CH2:22][CH2:23][CH2:24][CH2:31][N:11]1[CH:12]=[CH:13][CH:14]=[C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:10]1=[O:15])=[N+:26]=[N-:27]

Participants

4

Reactant 3

HCID 156664523-(Benzyloxy)pyridin-2-olHCID 866750842-Azidobutyl methanesulfonateHCID 866750871-(2-Azidoethyl)-3-methoxypyridine-2-one

Product 1

HCID 711399151-(4-Azidobutyl)-3-benzyloxypyridine-2-oneYield 62%

Procedure

Reaction of 3-benzyloxypyridine-2-one (0.40 g, 1.99 mmol) and 156c (0.58 g, 2.98 mmol) within 16 h as described for synthesis of 157a gave compound 157c (0.36 g, 62%) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 7.22 (m, 5H), 6.78 (dd, J=6.9, 1.7 Hz, 1H), 6.54 (dd, J=7.4, 1.7 Hz, 1H), 5.91 (m, 1H), 4.96 (s, 2H), 3.85 (t, J=7.2 Hz, 2H), 3.17 (t, J=6.8 Hz, 2H), 1.71 (m, 2H), 1.48 (m, 2H). 13C NMR (100 MHz, CDCl3) δ 157.52, 148.27, 135.78, 128.37, 127.98, 127.42, 126.82, 114.92, 104.32, 70.09, 50.43, 48.46, 25.83, 25.42. HRMS (EI) calcd for C16H18N4O2 [M]+ 298.1430. found 298.1446.

Sources & evidence

ORD record
ord-14ddd469b6154303997269359812614b
Source dataset
uspto-grants-2014_10
Patent number
US08871728B2

Reaction notes

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