Potassium Iodide → HCID 68512865, compound

HRID 1621997Notes

Reaction equation

Br[CH:2]([C:4]1[CH:5]=[CH:6][C:7]([F:10])=[N:8][CH:9]=1)[CH3:3].C(#N)C.[C:14]([N:21]1[CH2:26][CH2:25][NH:24][C@H:23]([CH3:27])[CH2:22]1)([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>O.C(Cl)Cl>[F:10][C:7]1[N:8]=[CH:9][C:4]([CH:2]([N:24]2[CH2:25][CH2:26][N:21]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:22][C@H:23]2[CH3:27])[CH3:3])=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a 100 mL round-bottomed flask was added 5-(1-bromoethyl)-2-fluoropyridine (3.9 g, 19.11 mmol), acetonitrile (75 mL, 1435 mmol), (R)-4-N-boc-2-methyl-piperazine (4.02 g, 20.07 mmol), (Aldrich), potassium carbonate (1.384 mL, 22.94 mmol), (Aldrich), potassium iodide (0.205 mL, 3.82 mmol), (Fluka). The reaction mixture was stirred at 70° C. overnight. The reaction mixture was diluted with water (50 mL) and DCM (50 mL) and extracted with DCM (3×50 mL) dried over sodium sulfate, filtered and concentrated under a vacuum to give (3R)-tert-butyl 4-(1-(6-fluoropyridin-3-yl)ethyl)-3-methylpiperazine-1-carboxylate (3.05 g, 9.43 mmol, 49.3% yield). The crude product was adsorbed onto a plug of silica gel and chromatographed through a silica gel column (80 g), eluting with a gradient of 0% to 50% EtOAc in hexane, to provide (3R)-tert-butyl 4-(1-(6-fluoropyridin-3-yl)ethyl)-3-methylpiperazine-1-carboxylate (3.05 g, 9.43 mmol, 49.3% yield).

Workup

extractionextracted with DCM (3×50 mL)
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated under a vacuum

Sources & evidence

ORD record: ord-700755d719c04f1fb551f68c770c46e1
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772480B2

Reaction notes

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