3-(Benzyloxy)pyridin-2-ol → (3-Azidopropyl)-3-benzyloxypyridine-2-one

HRID 539535Notes

Reaction equation

HRID 539535 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(O[CH2:21][CH:22]([N:24]=[N+:25]=[N-:26])C)(=O)=O.N([CH2:30]CN1C=CC=C(OC)C1=O)=[N+]=[N-]>>[N:24]([CH2:22][CH2:21][CH2:30][C:14]1[CH:13]=[CH:12][NH:11][C:10](=[O:15])[C:9]=1[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[N+:25]=[N-:26]

Participants

4

Reactant 3

HCID 156664523-(Benzyloxy)pyridin-2-olHCID 866750871-(2-Azidoethyl)-3-methoxypyridine-2-oneHCID 893069592-Azidopropyl methanesulfonate

Product 1

HCID 71139397(3-Azidopropyl)-3-benzyloxypyridine-2-oneYield 53%

Procedure

Reaction of 3-benzyloxypyridine-2-one (0.40 g, 1.99 mmol) and 156b (0.53 g, 2.98 mmol) within 16 h as described for synthesis of 157a gave compound 157b (0.30 g, 53%) as a colorless oil. 1H NMR (300 MHz, CDCl3) 7.28 (m, 5H), 6.84 (dd, J=6.9, 1.6 Hz, 1H), 6.60 (dd, J=7.4, 1.5 Hz, 1H), 5.98 (t, J=7.1 Hz, 1H), 3.97 (t, J=6.8 Hz, 2H), 3.28 (t, J=6.5 Hz, 2H), 1.98 (p, J=6.7 Hz, 2H). 13C NMR (75 MHz, CDCl3) δ 157.78, 148.65, 135.93, 128.85, 128.24, 127.69, 127.03, 115.16, 104.53, 70.39, 48.14, 47.06, 27.66. HRMS (EI) calcd for C15H16N4O2 [M]+ 284.1273. found 284.1271.

Sources & evidence

ORD record
ord-1ace30851ee44ff2a3559f8754f8aa89
Source dataset
uspto-grants-2014_10
Patent number
US08871728B2

Reaction notes

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