5-Fluoropyridine-2-carboxaldehyde → (S)-N-[(5-Fluoropyridin-2-yl)methylene]-2-methylpropane-2-sulfinamide

HRID 450381Notes

Reaction equation

HRID 450381 reaction equation
[Si](O[CH2:9][CH:10]=[N:11][S@@:12]([C:14]([CH3:17])([CH3:16])[CH3:15])=[O:13])(C(C)(C)C)(C)C.[F:18][C:19]1[CH:20]=[CH:21]C(C=O)=[N:23][CH:24]=1.CC([S@@](N)=O)(C)C>>[F:18][C:19]1[CH:20]=[CH:21][C:9]([CH:10]=[N:11][S@:12]([C:14]([CH3:15])([CH3:16])[CH3:17])=[O:13])=[N:23][CH:24]=1

Participants

4

Reactant 3

HCID 103516975-Fluoropyridine-2-carboxaldehydeHCID 11355477tert-Butylsulfinamide, (S)-(-)-HCID 86644143(R,E)-N-(2-((tert-butyldimethylsilyl)oxy)ethylidene)-2-methylpropane-2-sulfinamide

Product 1

HCID 68781418(S)-N-[(5-Fluoropyridin-2-yl)methylene]-2-methylpropane-2-sulfinamide

Procedure

The title compound was prepared using a procedure similar to the one described for the synthesis of Intermediate 21, using 5-fluoropyridine-2-carbaldehyde and (S)-2-methylpropane-2-sulfinamide as the starting materials. 1H NMR (300 MHz, CDCl3) δ ppm 8.67 (s, 1H) 8.58 (s, 1H) 8.06 (dd, J=8.29, 4.52 Hz, 1H) 7.51 (t, J=7.91 Hz, 1H) 1.20-1.33 (m, 9H). The product was used without purification.

Workup

  1. customThe product was used without purification

Sources & evidence

ORD record
ord-99a4d028f36e46bbbbdb985736756c2b
Source dataset
uspto-grants-2013_07
Patent number
US08486966B2

Reaction notes

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