Cesium carbonate → HCID 118253147, compound

HRID 1770797Notes

Reaction equation

Cl[CH2:2][C:3]1[C:4]([N:9]2[CH2:15][CH:14]3[O:16][CH:11]([CH2:12][CH2:13]3)[CH2:10]2)=[N:5][CH:6]=[CH:7][CH:8]=1.[OH:17][C:18]1[C:27]2[C:26](=[O:28])[O:25][C:24]([CH3:30])([CH3:29])[O:23][C:22]=2[CH:21]=[CH:20][CH:19]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH:11]12[O:16][CH:14]([CH2:13][CH2:12]1)[CH2:15][N:9]([C:4]1[C:3]([CH2:2][O:17][C:18]3[C:27]4[C:26](=[O:28])[O:25][C:24]([CH3:30])([CH3:29])[O:23][C:22]=4[CH:21]=[CH:20][CH:19]=3)=[CH:8][CH:7]=[CH:6][N:5]=1)[CH2:10]2

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of provide 3-(3-(chloromethyl)pyridin-2-yl)-8-oxa-3-azabicyclo[3.2.1]octane (0.080 g, 0.35 mmol) and 5-hydroxy-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one (0.061 g, 0.31 mmol) in DMF was added cesium carbonate (0.307 g, 0.94 mmol) and the reaction mixture was heated (60° C.). After 30 minutes, the reaction mixture was partitioned between EtOAc and saturated aqueous sodium bicarbonate and the aqueous layer was extracted two times with EtOAc. Combined organic layers were washed with brine, dried over MGSO4 and concentrated in vacuo. Purification by silica gel chromatography yielded 5-((2-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyridin-3-yl)methoxy)-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one (112 mg, 90% yield). MS (ES) for C22H24N2O5: 397 (MH+).

Workup

customthe reaction mixture was partitioned between EtOAc and saturated aqueous sodium bicarbonate
extractionthe aqueous layer was extracted two times with EtOAc
washCombined organic layers were washed with brine
customdried over MGSO4
concentrationconcentrated in vacuo
customPurification by silica gel chromatography

Sources & evidence

ORD record: ord-745413fb6fe545deb57bbc5fd2084498
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09248199B2

Reaction notes

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