Cesium carbonate → 8-chloro-5H-chromeno[3,4-c]pyridin-5-one

HRID 870915Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([C:14]([OH:16])=[O:15])=[CH:12][N:11]=[CH:10][CH:9]=2)=[C:4](F)[CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CS(C)=O.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]2[C:8]3[C:13](=[CH:12][N:11]=[CH:10][CH:9]=3)[C:14](=[O:16])[O:15][C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 4-(4-chloro-2-fluorophenyl)nicotinic acid (0.3 g, 1.192 mmol) in anhydrous DMSO (1 mL) was added Cs2CO3 (0.388 g, 1.192 mmol) and the mixture was subjected to microwave heating for 2 h at 60° C. The reaction mixture was diluted with water and extracted with ethyl acetate (2×15 mL). The combined organic extracts were washed with water (1×15 mL) and brine (1×15 mL), dried over sodium sulfate and concentrated under reduced pressure to afford 8-chloro-5H-chromeno[3,4-c]pyridin-5-one (0.2 g, 0.863 mmol, 72% yield over 2 steps). 1H NMR (400 MHz, CDCl3) δ 9.57 (d, J=0.40 Hz, 1H), 8.98 (d, J=5.60 Hz, 1H), 8.01 (d, J=8.80 Hz, 1H), 7.88 (q, J=0.40 Hz, 1H), 7.44 (d, J=2.00 Hz, 1H), 7.39 (q, J=2.00 Hz, 1H); LCMS (ESI) m/e 232.6 [(M+H)+, calcd for C12H7ClNO2 232.0]; LCMS retention time (Method D): tR=0.81 min.

Workup

extractionextracted with ethyl acetate (2×15 mL)
washThe combined organic extracts were washed with water (1×15 mL) and brine (1×15 mL)
dry with materialdried over sodium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-65b8d836ac424f7386b8a8e64e62ec79
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969564B2

Reaction notes

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