Cesium carbonate → Methyl 1-cyclopentyl-6-oxo-5-(pyrrolidin-1-yl)-1,6-dihydropyridine-3-carboxylate

HRID 1696277Notes

Reaction equation

Br[C:2]1[C:7](=[O:8])[N:6]([CH:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)[CH:5]=[C:4]([C:14]([O:16][CH3:17])=[O:15])[CH:3]=1.[NH:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH:9]1([N:6]2[C:7](=[O:8])[C:2]([N:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)=[CH:3][C:4]([C:14]([O:16][CH3:17])=[O:15])=[CH:5]2)[CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

Conditions

Temperature: 95 °C

Procedure

A mixture of methyl 5-bromo-1-cyclopentyl-6-oxo-1,6-dihydropyridine-3-carboxylate (100 mg, 0.33 mmol), pyrrolidine (33 uL, 0.40 mmol), cesium carbonate (150 mg, 0.46 mmol), tris(dibenzylideneacetone)dipalladium (0) (3 mg, 0.0033 mmol), rac-2-2′-bis(diphenyl-phosphino)-1,1′-binaphthyl (3.1 mg, 0.005 mmol) was purged with nitrogen for 30 min, followed by the addition of anhydrous toluene (1.5 mL). The resulting light-brown solution was heated to 95° C. for 17. The mixture was brought to room temperature and partitioned between ethyl acetate and saturated NH4Cl. The organic phase was separated, washed with saturated NH4Cl, brine, dried over MgSO4 and chromatographed on silica gel using 3:1 hexanes:ethyl acetate to afford the title compound as a yellow oil. MS m/z: 291 (M+1).

Workup

customwas purged with nitrogen for 30 min
additionfollowed by the addition of anhydrous toluene (1.5 mL)
customwas brought to room temperature
custompartitioned between ethyl acetate and saturated NH4Cl
customThe organic phase was separated
washwashed with saturated NH4Cl, brine
dry with materialdried over MgSO4
customchromatographed on silica gel using 3:1 hexanes

Sources & evidence

ORD record: ord-c4a24d4cfc06411988f71176d484cdb7
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163766B2

Reaction notes

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