Potassium Carbonate → HCID 59401842, compound

HRID 1916908Notes

Reaction equation

F[C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH3:8])[CH:7]=1.Cl.[CH3:13][C@@H:14]1[CH2:18][CH2:17][CH2:16][N:15]1[CH:19]1[CH2:23][CH2:22][NH:21][CH2:20]1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[CH3:13][C@@H:14]1[CH2:18][CH2:17][CH2:16][N:15]1[CH:19]1[CH2:23][CH2:22][N:21]([C:2]2[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH3:8])[CH:7]=2)[CH2:20]1

Participants

Conditions

Temperature: 85 °C

Procedure

5-Fluoro-2-nitrotoluene (1.55 g, 10 mmol) was dissolved in anhydrous DMSO. To this solution was added 2-(2R)-methyl-[1,3′]bipyrrolidinyl hydrochloride (2.30 g, 15 mmol), followed by powdered potassium carbonate. The suspension was heated on an oil bath to 85° C. for 3 h when the starting material was consumed as determined by TLC (5% MeOH/DCM) and LC/MS. To the suspension were added 20 mL of water and 50 mL of DCM. The two layers were separated, and the aqueous layer was extracted with DCM (20 mL×2). The combined DCM extracts were washed with sodium bicarbonate (20 mL), and brine (15 mL×2), dried (anhydrous potassium carbonate), filtered, and concentrated in vacuo. The crude product was purified on a silica gel column, eluted with 5% MeOH in DCM to get the title compound as a yellow solid after drying, 2.70 g (93%). MS: 290 (M+1).

Workup

customwas consumed
additionTo the suspension were added 20 mL of water and 50 mL of DCM
customThe two layers were separated
extractionthe aqueous layer was extracted with DCM (20 mL×2)
washThe combined DCM extracts were washed with sodium bicarbonate (20 mL), and brine (15 mL×2)
dry with materialdried (anhydrous potassium carbonate)
filtrationfiltered
concentrationconcentrated in vacuo
customThe crude product was purified on a silica gel column
washeluted with 5% MeOH in DCM

Sources & evidence

ORD record: ord-94a3bd5d8e5c46b0a33ea25ae8473672
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08618159B2

Reaction notes

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