2-(Pivaloylamino)pyridine → N-(3-isobutyrylpyridin-2-yl)pivalamide
Reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8](=[O:13])[C:9]([CH3:12])([CH3:11])[CH3:10].[Li]CCCC.CON(C)[C:22](=[O:26])[CH:23]([CH3:25])[CH3:24]>>[C:22]([C:3]1[C:2]([NH:7][C:8](=[O:13])[C:9]([CH3:10])([CH3:12])[CH3:11])=[N:1][CH:6]=[CH:5][CH:4]=1)(=[O:26])[CH:23]([CH3:25])[CH3:24]Participants
4
Procedure
A solution of N-(pyridin-2-yl)pivalamide (3.20 g, 18.0 mmol), n-BuLi (15.00 mL, 2.1 eq.) and N-methoxy-N-methylisobutyramide (2.60 g, 1.1 eq) were reacted as outlined in Scheme 1 to give 3.10 g (69%) of N-(3-isobutyrylpyridin-2-yl)pivalamide. Spectroscopic data: 1H NMR (300 MHz, CDCl3) δ ppm 1.21 (d, J=7.03 Hz, 6 H) 1.35 (s, 9 H) 3.55 (dt, J=13.70, 6.78 Hz, 1 H) 7.08 (dd, J=7.91, 4.69 Hz, 1 H) 8.19 (dd, J=8.20, 2.05 Hz, 1 H) 8.63 (dd, J=4.83, 1.90 Hz, 1 H) 11.51 (br. s., 1 H).
Sources & evidence
- ORD record
- ord-301e98587cde49488ebe13f1a6dc7c3a
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08703797B2
Reaction notes
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