Cesium carbonate → 7-[4-Methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-3,4-dihydro-1H-quinolin-2-one

HRID 490771Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of 7-hydroxy-3,4-dihydro-1H-quinolin-2-one (310 mg, 1.90 mmol) and 5-chloromethyl-4-methyl-2-(4-trifluoromethyl-phenyl)-thiazole (666 mg, 2.28 mmol) in DMF (3.0 mL) is treated with Cs2CO3 (1.25 g, 3.80 mmol). The resulting suspension is heated at 60° C. for 5 hours and then quenched with water dropwise. The mixture is extracted with EtOAc (40 mL×3) and the combined organics are dried (Na2SO4), concentrated to a suspension. It is then filtered and the solid is rinsed with EtOAc (2 mL) and dried under vacuum to obtain pure product (233 mg, 29%).

Workup

customquenched with water dropwise
extractionThe mixture is extracted with EtOAc (40 mL×3)
dry with materialthe combined organics are dried (Na2SO4)
concentrationconcentrated to a suspension
filtrationIt is then filtered
washthe solid is rinsed with EtOAc (2 mL)
customdried under vacuum

Sources & evidence

ORD record: ord-04b894bed77f4da1a89c246ce37abe2c
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07528160B2

Reaction notes

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