O-(Trimethylsilyl)hydroxylamine → 4-(5-bromopyridin-2-yl)-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide

HRID 533533Notes

Reaction equation

HRID 533533 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]([CH3:18])([S:14]([CH3:17])(=[O:16])=[O:15])[C:11](O)=[O:12])=[N:6][CH:7]=1.C[Si](C)(C)[O:21][NH2:22].BrC1C=CC(CCC(C)(S(C)(=O)=O)C(NO)=O)=CC=1>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]([CH3:18])([S:14]([CH3:17])(=[O:16])=[O:15])[C:11]([NH:22][OH:21])=[O:12])=[N:6][CH:7]=1

Participants

4

Reactant 3

HCID 2734666O-(Trimethylsilyl)hydroxylamineHCID 665778654-(5-Bromopyridin-2-yl)-2-methyl-2-(methylsulfonyl)butanoic acidHCID 86668754(+/-)-4-(4-Bromophenyl)-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide

Product 1

HCID 866687644-(5-bromopyridin-2-yl)-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamideYield 25%

Procedure

The title compound (454 mg, 25%) was prepared from 4-(5-bromopyridin-2-yl)-2-methyl-2-(methylsulfonyl)butanoic acid (1740 mg, 5.2 mmol) and O-(trimethylsilyl)hydroxylamine (1810 mg, 15.5 mmol) by a procedure analogous to that described for the preparation of compound (IV) 4-(6-Bromophenyl-3-yl)-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide from Preparation 2, Step 5. MS (LCMS) m/z 351.0 (M+1). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.70 (s, 3H) 2.17-2.38 (m, 1H) 2.52-2.68 (m, 1H) 2.70-2.85 (m, 1H) 2.85-2.96 (m, 1H) 3.00 (s, 3H) 7.09 (d, J=8.20 Hz, 1H) 7.76 (dd, J=8.20, 2.34 Hz, 1H) 8.58 (d, J=2.34 Hz, 1H).

Sources & evidence

ORD record
ord-618a68b5cc354ca9b41c817763d24592
Source dataset
uspto-grants-2014_10
Patent number
US08853258B2

Reaction notes

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