3-(Benzyloxy)pyridin-2-ol → 1-(7-Azidoheptyl)-3-benzyloxypyridine-2-one

HRID 539539Notes

Reaction equation

HRID 539539 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:28]=[N+:29]=[N-:30])[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])(=O)=O.N([CH2:34]CN1C=CC=C(OC)C1=O)=[N+]=[N-]>>[N:28]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:34][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+:29]=[N-:30]

Participants

4

Reactant 3

HCID 156664523-(Benzyloxy)pyridin-2-olHCID 866750871-(2-Azidoethyl)-3-methoxypyridine-2-oneHCID 866750882-Azidoheptyl methanesulfonate

Product 1

HCID 711388291-(7-Azidoheptyl)-3-benzyloxypyridine-2-oneYield 48%

Procedure

Reaction of 3-benzyloxypyridine-2-one (0.79 g, 3.38 mmol) and 156f (0.81 g, 4.05 mmol) within 16 h as described for synthesis of 157a gave compound 157f (0.55 g, 48%) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 7.42 (dd, J=7.8, 1.0 Hz, 2H), 7.31 (m, 3H), 6.85 (dd, J=6.9, 1.7 Hz, 1H), 6.61 (dd, J=7.4, 1.7 Hz, 1H), 5.99 (m, 1H), 5.09 (s, 2H), 3.93 (m, 2H), 3.23 (t, J=6.9 Hz, 2H), 1.74 (m, 2H), 1.55 (m, 2H), 1.34 (m, 6H). 13C NMR (100 MHz, CDCl3) δ 158.32, 149.19, 136.63, 129.15, 128.74, 128.13, 127.52, 115.66, 104.69, 94.66, 70.96, 51.62, 50.03, 29.22, 28.98, 26.77, 26.72.

Sources & evidence

ORD record
ord-40be95e4ea79408399bac7038c9e102a
Source dataset
uspto-grants-2014_10
Patent number
US08871728B2

Reaction notes

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