1-(6-Nitro-pyridin-3-yl)-azetidin-3-ol → 1-(6-Aminopyridin-3-yl)azetidin-3-ol

HRID 1772136Notes

Reaction equation

HRID 1772136 reaction equation
[Si](OCCN1C=CC(N)=N1)(C(C)(C)C)(C)C.[N+:17]([C:20]1[N:25]=[CH:24][C:23]([N:26]2[CH2:29][CH:28]([OH:30])[CH2:27]2)=[CH:22][CH:21]=1)([O-])=O>>[NH2:17][C:20]1[N:25]=[CH:24][C:23]([N:26]2[CH2:27][CH:28]([OH:30])[CH2:29]2)=[CH:22][CH:21]=1

Participants

3

Reactant 2

HCID 592909581-(6-Nitro-pyridin-3-yl)-azetidin-3-olHCID 593449471-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1H-pyrazol-3-ylamine

Product 1

HCID 580438121-(6-Aminopyridin-3-yl)azetidin-3-olYield 95.1%

Procedure

Using the same general procedure for the preparation of 119b, reduction of 120a (1.43 g, 7.32 mmol) gave a 95% yield (1.15 g) of 120b as a yellow semi-solid: 1H NMR (500 MHz, DMSO-d6) δ 7.22 (d, 1H, J=2.5 Hz), 6.69 (m, 1H), 6.35 (d, 1H, J=8.0 Hz), 5.16 (s, 1H), 4.48 (m, 1H), 3.96 (m, 2H), 3.34 (m, 2H); MS (ESI+) m/z 166.2 (M+H).

Sources & evidence

ORD record
ord-b90b6e90d8d444469d3d6510e68b6bbe
Source dataset
uspto-grants-2016_02
Patent number
US09249123B2

Reaction notes

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