Water → HCID 58805181, compound

HRID 349709Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[CH:5]=[C:4]([OH:14])[C:3]=1[C:15](=[O:17])[CH3:16].C([O-])([O-])=O.[K+].[K+].Cl.[C:25](Cl)(=O)[C:26]1[CH:31]=[CH:30][CH:29]=[N:28][CH:27]=1.O>CC(C)=O>[OH:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[CH:5]=[C:4]2[C:3]=1[C:15](=[O:17])[CH:16]=[C:25]([C:26]1[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=1)[O:14]2

Participants

Conditions

Temperature: 85 °C

Procedure

To a suspension of 1-(2,6-dihydroxy-4-morpholin-4-yl-phenyl)-ethanone (86 mg, 0.362 mmol) and K2CO3 (250 mg, 1.81 mmol) in acetone (3 mL) was added nicotinoyl chloride hydrochloride (0.71 mL, 0.399). The reaction vessel was sealed and heated to 85° C. for 24 h. After cooling to room temperature, water (about 2 mL) was added, and the mixture was allowed to stir for about 10 min. The contents were transferred to a separatory funnel containing water (5 mL) and extracted with EtOAc (3×15 mL). The organic layer was dried (MgSO4) and concentrated. The concentrate was purified via Biotage chromatography with gradient elution from 100% hexanes to 100% EtOAc to yield 14 mg (12%) of 5-hydroxy-7-morpholin-4-yl-2-pyridin-3-yl-chromen-4-one. Rf=0.22 (100% EtOAc).

Workup

customThe reaction vessel was sealed
temperatureAfter cooling to room temperature
customThe contents were transferred to a separatory funnel
extractionextracted with EtOAc (3×15 mL)
dry with materialThe organic layer was dried (MgSO4)
concentrationconcentrated
customThe concentrate was purified via Biotage chromatography with gradient elution from 100% hexanes to 100% EtOAc

Sources & evidence

ORD record: ord-0634eeee084e4d1fa70e225dd840baea
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07179912B2

Reaction notes

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