2,6-Difluoropyridine → HCID 57430079, compound

HRID 1169840Notes

Reaction equation

HRID 1169840 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[N:3]=1.[C:9]([CH:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]1)#[N:10].C[Si](C)(C)[N-][Si](C)(C)C.[K+]>>[C:9]([C:11]1([C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[N:3]=2)[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]1)#[N:10]

Participants

4

Reactant 3

HCID 739342,6-DifluoropyridineHCID 1514443Tert-butyl 4-cyanopiperidine-1-carboxylateHCID 3251421Potassium bis(trimethylsilyl)amide

Product 1

HCID 57430079HCID 57430079, compound

Procedure

2,6-Difluoropyridine (2 g, 17 mmol) and tert-butyl 4-cyanopiperidine-1-carboxylate (2.4 g, 11 mmol) were reacted in the presence of potassium hexamethyldisilazide (14 mmol) using the method described in example 8-1 to afford the desired product: tert-butyl 4-cyano-4-(6-fluoropyridin-2-yl)piperidine-1-carboxylate: 1H NMR δ (ppm)(CDCl3): 7.86 (1 H, q, J=7.9 Hz), 7.54 (1 H, dd, J=2.3, 7.4 Hz), 6.93-6.91(1 H, m), 4.28 (21H, br s), 3.17 (2 H, br s), 2.25-2.17 (2 H, m), 2.02 (2 H, d, J=14.6 Hz), 1.48 (9H, s).

Sources & evidence

ORD record
ord-14f6769ce0334e66bbb797e26e79b014
Source dataset
uspto-grants-2010_11
Patent number
US07825135B2

Reaction notes

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